[ CAS No. 269409-70-3 ] {[proInfo.proName]}

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Quality Control of [ 269409-70-3 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 269409-70-3 ]

Product Citations

Spontaneous Symmetry Breaking in Polar Fluids

Calum Gibb ; Jordan Hobbs ; Diana Nikolova , et al. arXiv,2024,7305.

Abstract: Spontaneous symmetry breaking and emergent polar order are each of fundamental importance to a range of scientific disciplines, as well as generating rich phase behaviour in liquid crystals (LCs). Here, we show the union of these phenomena to lead to two previously undiscovered polar liquid states of matter. Both phases have a lamellar structure with an inherent polar ordering of their constituent molecules. The first of these phases is characterised by polar order and a local tilted structure; the tilt direction precesses about a helix orthogonal to the layer normal, the period of which is such that we observe selective reflection of light. The second new phase type is anti-ferroelectric, with the constituent molecules aligning orthogonally to the layer normal. This has led us to term the phases the SmC_P^H and SmAAF phases, respectively. Further to this, we obtain room temperature ferroelectric nematic (NF) and SmC_P^Hphases via binary mixture formulation of the novel materials described here with a standard NF compound (DIO), with the resultant materials having melting points (and/or glass transitions) which are significantly below ambient temperature.

Purchased from AmBeed: 269409-70-3 ; 511540-64-0

Product Details of [ 269409-70-3 ]

CAS No. :	269409-70-3	MDL No. :	MFCD02093756
Formula :	C₁₂H₁₇BO₃	Boiling Point :	No data available
Linear Structure Formula :	(C₃H₆O)₂BC₆H₄OH	InChI Key :	BICZJRAGTCRORZ-UHFFFAOYSA-N
M.W :	220.07	Pubchem ID :	2734624
Synonyms :		Chemical Name :	4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenol

Calculated chemistry of [ 269409-70-3 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.5
Num. rotatable bonds :	1
Num. H-bond acceptors :	3.0
Num. H-bond donors :	1.0
Molar Refractivity :	64.94
TPSA :	38.69 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	Yes
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.83 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	2.55
Log Po/w (WLOGP) :	1.69
Log Po/w (MLOGP) :	1.13
Log Po/w (SILICOS-IT) :	1.35
Consensus Log Po/w :	1.35

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.02
Solubility :	0.209 mg/ml ; 0.00095 mol/l
Class :	Soluble
Log S (Ali) :	-3.01
Solubility :	0.215 mg/ml ; 0.000978 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.43
Solubility :	0.082 mg/ml ; 0.000372 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.82

Safety of [ 269409-70-3 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P305+P351+P338	UN#:
Hazard Statements:	H315-H319-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 269409-70-3 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 269409-70-3 ]
Downstream synthetic route of [ 269409-70-3 ]

[ 269409-70-3 ] Synthesis Path-Upstream 1~1

1
[ 1895-39-2 ]
[ 269409-70-3 ]
[ 1333222-12-0 ]

Yield	Reaction Conditions	Operation in experiment
53%	at 80℃; Sealed tube	In a sealed tube was added 2-hydroxy-5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)pyridine (300 mg, 1.357 mmol), sodium chlorodifluoroacetate (320 mg, 2.036 mmol) in acetonitrile (5 mL). This suspension was heated to 80°C and stirred overnight. The reaction mixture was cooled down to rt, diluted with EtOAc, washed with an aqueous solution of NaHC0₃ and brine. The organic layer dried over MgS0₄, filtered and evaporated. Purification by flash chromatography on silica gel (CH2CI2/MeOH, 95/5) gave the title compound (197 mg, 53percent yield). MS: 272.8 [M+H]⁺, Rt ⁽⁶⁾ = 3.12 min.

Reference： [1] Patent: WO2013/88404, 2013, A1, . Location in patent: Page/Page column 96

[ 269409-70-3 ] Synthesis Path-Downstream 1~9

1
[ 1001756-23-5 ]
[ 269409-70-3 ]
[ 1276656-22-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate;palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 60℃; for 1h;	2d) Methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate A solution of 78 mg (0.29 mmol) of <strong>[1001756-23-5]methyl 7-bromo-3-quinolinecarboxylate</strong>, 97 mg (0.44 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol, 3 mg (0.01 mmol) of palladium acetate, 8 mg (0.03 mmol) of triphenylphosphine, 218 mg (1.03 mmol) of K3PO4 and 25 muL of H2O in 1.0 mL of dioxane was stirred at 60° C. for 1 hr. EtOAc was added and the organics were washed with water and brine then concentrated. To the residue was added 65 mg (0.21 mmol) of 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole, 74 mg (0.54 mmol) of K2CO3 and 1.5 mL of DMF and the mixture was then stirred at 60° C. for 1 hr. EtOAc was added and the organics were washed with three portions of water, then brine. The solution was concentrated and the residue purified by silica gel chromatography (12 g of silica gel eluding with 0-40percent EtOAc in hexanes over 45 minutes) to give 47 mg (30percent) of methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate as a clear glass. 1H NMR (400 MHz, CDCl3): delta 9.44 (s, 1H), 8.83 (s, 1H), 8.28 (s, 1H), 7.96 (d, J=9 Hz, 1H), 7.82 (d, J=9 Hz, 1H), 7.64 (d, J=9 Hz, 2H), 7.41 (d, J=8 Hz, 2H), 7.35-7.31 (m, 1H), 6.92 (d, J=9 Hz, 2H), 4.79 (s, 2H), 4.02 (s, 3H), 3.38-3.34 (m, 1H), 1.45 (d, J=7 Hz, 6H). ESI-LCMS m/z 548 (M+H)+.
	With potassium phosphate; palladium diacetate; triphenylphosphine; In 1,4-dioxane; water; at 60℃; for 1h;	A solution of <strong>[1001756-23-5]methyl 7-bromo-3-quinolinecarboxylate</strong> 2c (78 mg, 0.29 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol 3b (97 mg, 0.44 mmol), palladium(II) acetate (3 mg, 0.01 mmol), triphenylphosphine (8 mg, 0.03 mmol), potassium phosphate (218 mg, 1.03 mmol), and water (25 muL) in dioxane (1.0 mL) was stirred at 60 °C for 1 hour. Ethyl acetate was added and the organics were washed with water and brine, and then concentrated to give methyl 7-(4-hydroxyphenyl)quinoline-3-carboxylate 4c. To methyl 7-(4-hydroxyphenyl)quinoline-3-carboxylate 4c was added 4-(chloromethyl)-3-(2,6-dichlorophenyl)-5-(1-methylethyl)isoxazole 5a (65 mg, 0.21 mmol), potassium carbonate (74 mg, 0.54 mmol) and N,N-dimethylformamide (1.5 mL) and the mixture was then stirred at 60 °C for 1 hour. Ethyl acetate was added and the organics were washed with three portions of water, then brine. The solution was concentrated, and the residue was purified by silica gel chromatography (hexanes to 2:3 ethyl acetate:hexanes) to give methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate (47 mg, 30percent) as a clear glass (1H NMR (400 MHz, CDCl3): 9.44 (s, 1H), 8.83 (s, 1H), 8.28 (s, 1H), 7.96 (d, J = 9 Hz, 1H), 7.82 (d, J = 9 Hz, 1H), 7.64 (d, J = 9 Hz, 2H), 7.41 (d, J = 8 Hz, 2H), 7.35-7.31 (m, 1H), 6.92 (d, J = 9 Hz, 2H), 4.79 (s, 2H), 4.02 (s, 3H), 3.38-3.34 (m, 1H), 1.45 (d, J = 7 Hz, 6H); ESI-LCMS m/z 548 (M+H)). To methyl 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylate (47 mg, 0.09 mmol) in a mixture of ethanol (3 mL), tetrahydrofuran (1 mL), and water (1 mL) was added sodium hydroxide (35 mg, 0.86 mmol) and the mixture stirred at 50 °C for 16 hours. The mixture was concentrated to 1/3 volume then added dropwise to a stirred solution of 0.5 N hydrochloric acid (10 mL). The resulting solids were collected by suction filtration, washed with water, then dried to yield 7-[4-([3-(2,6-dichlorophenyl)-5-(1-methylethyl)-4-isoxazolyl]methyl}oxy)phenyl]-3-quinolinecarboxylic acid 1e (32 mg, 70percent) as a yellow solid. 1H NMR (400 MHz, DMSO-d6): delta 9.30 (s, 1H), 8.97 (s, 1H), 8.24-8.21 (m, 2H), 7.99 (d, J = 8 Hz, 1H), 7.76 (d, J = 8 Hz, 2H), 7.63-7.61 (m, 2H), 7.55-7.52 (m, 1H), 6.93 (d, J = 9 Hz, 2H), 4.88 (s, 2H), 3.50-3.44 (septet, J = 7 Hz, 1H), 1.33 (d, J = 7 Hz, 6H); ESI-LCMS m/z 534 (M+H).

Reference： [1]Patent: US2008/96921,2008,A1 .Location in patent: Page/Page column 35-36
[2]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 1206 - 1213

2
[ 4805-22-5 ]
[ 269409-70-3 ]
[ 185413-64-3 ]

Yield	Reaction Conditions	Operation in experiment
84%	With tetraethylammonium hydroxide;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; for 5h;Heating / reflux;	Example 1 Compound (1) is prepared as follows : Step 1.1 : 2. 5'-Bis (4-hvdroxyphenYl) bithiophene.; To a solution of 5, 5'-dibromo-2, 2'-bithiophene (5.0 g, 15.43 mmol) in anhydrous THF (120 ml) is added tetrakis (triphenylphosphine) palladium (0.5 g, 0.43 mmol). This mixture is degassed with nitrogen for 20 min, followed by the addition of 4- (4, 4,5, 5-tetramethyl [1, 3,2] dioxoborolan-2-yl)-phenol (3.73 g, 16.95 mmol, Aldrich) and tetraethylamomnium hydroxide (20% solution in water, 50 ml). The mixture is heated at reflux for 5 h. After cooling, 1 M HCI solution (70 mt) is added and the precipitate is filtered off then washed with water (3 x 20 ml) and dried, to give a green solid (4.52 g, 84 %). NMR showed the expected signals.

Reference： [1]Patent: WO2005/80369,2005,A2 .Location in patent: Page/Page column 28-29

3
[ 240800-45-7 ]
[ 269409-70-3 ]
[ 1367127-42-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃;	Compound 5d: A mixture of compound 6 (2.1 g, 10.9 mmol), compound 7 (2.4g, 10.9 mmol) and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was filtered through a plug of silica gel and the plug was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was purified by column chromatography (40 g silica gel, 0-30% EtOAc/Hexane) to obtain compound 5d (2.3 g, 6.9 mmol). 1H NMR (400MHz, CD3OD): 7.81 (d, 2H, J=8.8Hz), 7.63 (d, 1H, J=8.8Hz), 7.26 (d, 1H, J=2.4Hz), 7.17 (dd, 1H, Jl=2.4, J2=8.8Hz), 6.98 (d, 2H, J=8.8Hz), 1.28 (s, 12H).
2.3 g	With caesium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 4.0h;	[0323] (c) Compound 12 was prepared as follows:[0324] A mixture of compound 16 (2.1 g, 10.9 mmol), compound 17 (2.4g, 10.9 mmol) and Cs2C03 (3.5 g, 10.9 mmol) in DMF (14 mL) was heated at 100C for 4 hours. After cooling to room temperature, the mixture was filtered through a plug of silica gel and the plug was washed with EtOAc (50 mL). The filtrate was concentrated and the residue was purified by column chromatography (40 g silica gel, 0-30% EtOAc/Hexane) to obtain compound 12 (2.3 g, 6.9 mmol). ? NMR (400MHz, CD3OD): ? 7.81 (d, 2H, J=8.8Hz), 7.63 (d, 1H, J=8.8Hz), 7.26 (d, 1H, J=2.4Hz), 7.17 (dd, 1H, Jl=2.4, J2=8.8Hz), 6.98 (d, 2H, J=8.8Hz), 1.28 (s, 12H).

Reference： [1]Patent: WO2012/35421,2012,A2 .Location in patent: Page/Page column 246-247
[2]Patent: WO2013/64883,2013,A1 .Location in patent: Paragraph 0323; 0324

4
[ 240800-45-7 ]
[ 269409-70-3 ]
[ 1433051-89-8 ]

Reference： [1]Patent: WO2013/64883,2013,A1

5
[ 19748-66-4 ]
[ 269409-70-3 ]
1-isopropyl-3-methyl-8-[4-(3-pyrrolidinpropoxy)phenyl]imidazo[4,5-c]quinolin-2-one [ No CAS ]

Reference： [1]Patent: WO2017/76895,2017,A1

6
[ 19748-66-4 ]
[ 269409-70-3 ]
1-[3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]propyl]pyrrolidine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
27%	With di-isopropyl azodicarboxylate; triphenylphosphine; In tetrahydrofuran; at 0 - 25℃; for 18h;Inert atmosphere;	l-[3-[4-(4,4,5,5-Tetramethyl-l,3,2-dioxaborolan-2-yl)phenoxy]propyl]pyrrolidine can also be prepared as follows: Diisopropylazodicarboxylate (6.71 mL, 34.08 mmol) was added dropwise to 4-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)phenol (5.00 g, 22.72 mmol), triphenylphosphine (8.94 g, 34.08 mmol) and 3-(pyrrolidin-l-yl)propan-l-ol (4.40 g, 34.08 mmol) in THF (50 mL) at 0°C under nitrogen. The resulting mixture was allowed to warm up to room temperature and stirred for 18 h. The reaction mixture was evaporated to afford yellow oil. The yellow oil was triturated from heptane/EtOAc (80/20), and the white solid was filtered off. The filtrate was concentrated and the crude product was purified by FCC, elution gradient 0 to 100percent EtOAc in heptane. Pure fractions were evaporated to dryness to afford the desired material as a pale yellow gum (2.05 g, 27 percent>). 'H NMR (500MHz, DMSO-d6) delta 1.13 (2H, t), 1.28 (12H, s), 1.68 (4H, dq), 1.79 - 1.96 (2H, m), 2.46 - 2.56 (4H, m), 3.94 - 4.11 (2H, m), 6.83 - 6.97 (2H, m), 7.58 - 7.66 (2H, m). Mass Spectrum: m/z (ES+)[M+H]+ not observed.

Reference： [1]Patent: WO2017/76895,2017,A1 .Location in patent: Page/Page column 48

7
[ 109431-87-0 ]
[ 269409-70-3 ]
tert-butyl (3S)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]pyrrolidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
100%	With diamide; triphenylphosphine; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere;	To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenol (a) (82.7 g, 364.51 mmol) in THF (2 L) was added under argon (R)-1-N-Boc-3-hydroxypyrrolidine (b) (84.43 g, 437.41 mmol) followed by N,N,N′,N′-tetramethylazodicarboxamide (99.1 g, 546.77 mmol). The clear reaction mixture turned orange and triphenylphosphine (143.41 g, 546.77 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours, meanwhile a precipitate of triphenylphosphine oxide formed (Ph3P═O). The reaction mixture was poured in water (1.5 L) and extracted with ethyl acetate (AcOEt) (3×1.5 L). Gathered organic phases were dried over magnesium sulfate (MgSO4), filtered and concentrated under reduced pressure. The residue was taken up into diisopropylether (1.5 L) and the solid formed (Ph3P═O) was filtered. The solvent was concentrated under reduced pressure and the residue purified by column chromatography eluting with a mixture of heptane with AcOEt (90/10; v/v) to give 145 g (100%) of tert-butyl (3S)-3-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy]pyrrolidine-1-carboxylate (c) as a colorless oil. 1H NMR (400 MHz, DMSO-d6, δ ppm): 1.27 (s, 12H); 1.39 (s, 9H); 2.05 (m, 1H); 2.14 (m, 1H); 3.37 (3H); 3.55 (m, 1H); 5.05 (s, 1H); 6.94 (d, J=8.4 Hz, 2H); 7.61 (d, J=8.4 Hz, 2H)
100%	With diamide; triphenylphosphine; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere;	To a solution of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenol (82.7 g, 364.51 mmol) in THF (2 L) was added under argon (R)-1 -N-Boc-3-hydroxypyrrolidine (84.43 g, 437.41 mmol) followed by Ν,Ν,Ν',Ν'-tetramethylazodicarboxamide (99.1 g, 546.77 mmol). The clear reaction mixture turned orange and triphenylphosphine (143.41 g, 546.77 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours, meanwhile a precipitate of triphenylphosphine oxide formed (Ph3P=0). The reaction mixture was poured in water (1 .5 L) and extracted with EtOAc (3x1 .5 L). Gathered organic phases were dried over magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was taken up into diisopropyl ether (1 .5 L) and the solid formed (Ph3P=0) was filtered. The solvent was concentrated under reduced pressure and the residue purified by column chromatography eluting with a mixture of heptane and EtOAc (90/10; v/v) to give 145 g (100%) of tert-butyl (3S)-3-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenoxy]pyrrolidine-1 -carboxylate (c) as a colorless oil. LC/MS (m/z, MH+): 390
100%	With diamide; triphenylphosphine; In tetrahydrofuran; at 20℃; for 24h;Inert atmosphere;	To a solution of 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)phenol (a) (82.7 g, 364.51 mmol) in THF (2 L) was added under argon (R)-1 -N-Boc-3-hydroxypyrrolidine (b) (84.43 g, 437.41 mmol) followed by N,N,N',N'-tetramethylazodicarboxamide (99.1 g, 546.77 mmol). The clear reaction mixture turned orange and triphenylphosphine (143.41 g, 546.77 mmol) was added. The reaction mixture was stirred at room temperature for 24 hours, meanwhile a precipitate of triphenylphosphine oxide formed (Phi3P=0). The reaction mixture was poured in water (1 .5 L) and extracted with ethyl acetate (AcOEt) (3x1 .5 L). Gathered organic phases were dried over magnesium sulfate (MgS04), filtered and concentrated under reduced pressure. The residue was taken up into diisopropylether (1 .5 L) and the solid formed (Pfi3P=0) was filtered. The solvent was concentrated under reduced pressure and the residue purified by column chromatography eluting with a mixture of heptane with AcOEt (90/10; v/v) to give 145 g (100%) of tert-butyl (3S)-3-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)phenoxy]pyrrolidine-1 -carboxylate (c) as a colorless oil. (0121) 1H NMR (400 MHz, DMSO-d6, d ppm): 1 .27 (s, 12H); 1.39 (s, 9H); 2.05 (m, 1 H); 2.14 (m, 1 H); 3.37 (3H); 3,55 (m, 1 H); 5.05 (s, 1 H); 6.94 (d, J = 8.4 Hz, 2H); 7.61 (d, J = 8.4 Hz, 2H).

1.76 g

With triphenylphosphine; diethylazodicarboxylate; In tetrahydrofuran; at 0 - 20℃;

In Step 1, Compound 54 (1g) was reacted with Compound 55 using PPh3 and DEAD in THF. The reaction was cooled to 0 C and allowed to warm to room temperature while stirring overnight. Following purification, Compound 56 (1.76 g) was obtained. In Step 2, Compound 56 (1.7 g) was subjected to deprotection conditions using TFA in DCM. The reaction stirred for 2 hours at room temperature and was purified to afford Compound 57 (1.25 g). In Step 3, Compound 57 (200 mg, 1 eq.) was dissolved in DMF and reacted with 1-fluoro-3-iodopropane (1.2 eq.) in the presence of K2CO3 (3 eq.). The reaction was heated to 110 C and allowed to stir overnight. Purification afforded Compound 58 (70 mg). Compound 58 (70 mg, 1 eq.) was then coupled to Compound 59 using Pd(PPh3)4 and K2CO3 in dioxane. The reaction was heated to 110 C and allowed to stir overnight. Following purification, 95 mg of Compound 60 was obtained. The 1HNMR was indicative of product. In Step 5, Compound 60 was subjected to hydrogenolysis. Compound 60 (90 mg) was dissolved in CH3COOH and MeOH and Ph(OH)2 was added. Following hydrogenolysis at 60 C for 2 hours and purification, Compound 108 (14.8 mg) was obtained.1HNMR, LC-MS, and HPLC were indicative of Compound 108.

Reference： [1]Patent: US9714221,2017,B1 .Location in patent: Page/Page column 191; 192; 193
[2]Patent: WO2018/91153,2018,A1 .Location in patent: Page/Page column 148
[3]Journal of Medicinal Chemistry,2020,vol. 63,p. 512 - 528
[4]Patent: WO2020/49150,2020,A1 .Location in patent: Page/Page column 17; 18
[5]Patent: WO2020/37251,2020,A1 .Location in patent: Page/Page column 148; 153-154

8
[ 118591-58-5 ]
[ 269409-70-3 ]
2-(2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenoxy)ethoxy)ethanol [ No CAS ]

Reference： [1]Patent: US2018/177750,2018,A1 .Location in patent: Paragraph 1106

9
[ 162709-84-4 ]
[ 269409-70-3 ]
4,4,5,5-tetramethyl-2-(4-((3,4,5-tris(dodecyloxy)benzyl)oxy)phenyl)-1,3,2-dioxaborolane [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2021,vol. 143,p. 5845 - 5854

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Technical Information

? Acidity of Phenols ? Acyl Group Substitution ? Benzylic Oxidation ? Birch Reduction ? Blanc Chloromethylation ? Bouveault-Blanc Reduction ? Catalytic Hydrogenation ? Chan-Lam Coupling Reaction ? Complex Metal Hydride Reductions ? Electrophilic Substitution of the Phenol Aromatic Ring ? Ester Cleavage ? Etherification Reaction of Phenolic Hydroxyl Group ? Friedel-Crafts Reaction ? Halogenation of Phenols ? Hydrogenolysis of Benzyl Ether ? Oxidation of Phenols ? Pechmann Coumarin Synthesis ? Preparation of Aldehydes and Ketones ? Preparation of Alkylbenzene ? Reactions of Benzene and Substituted Benzenes ? Reactions with Organometallic Reagents ? Reimer-Tiemann Reaction ? Specialized Acylation Reagents-Carbodiimides and Related Reagents ? Vilsmeier-Haack Reaction

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