[ CAS No. 1054483-78-1 ] {[proInfo.proName]}

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Quality Control of [ 1054483-78-1 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 1054483-78-1 ]

SDS Specification

Alternatived Products of [ 1054483-78-1 ]

Product Details of [ 1054483-78-1 ]

CAS No. :	1054483-78-1	MDL No. :	MFCD06795671
Formula :	C₁₁H₁₆BNO₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	WAUWXCUPDOXYKS-UHFFFAOYSA-N
M.W :	221.06	Pubchem ID :	17750253
Synonyms :

Calculated chemistry of [ 1054483-78-1 ] Expand+

Physicochemical Properties

Num. heavy atoms :	16
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.55
Num. rotatable bonds :	1
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	62.74
TPSA :	51.58 ?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) :	-6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.0
Log Po/w (XLOGP3) :	1.82
Log Po/w (WLOGP) :	1.09
Log Po/w (MLOGP) :	0.41
Log Po/w (SILICOS-IT) :	0.82
Consensus Log Po/w :	0.83

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.57
Solubility :	0.597 mg/ml ; 0.0027 mol/l
Class :	Soluble
Log S (Ali) :	-2.52
Solubility :	0.663 mg/ml ; 0.003 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.06
Solubility :	0.194 mg/ml ; 0.000879 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.86

Safety of [ 1054483-78-1 ]

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

Application In Synthesis of [ 1054483-78-1 ]

* 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 [ 1054483-78-1 ]
Downstream synthetic route of [ 1054483-78-1 ]

[ 1054483-78-1 ] Synthesis Path-Upstream 1~1

1
[ 1054483-78-1 ]
[ 1895-39-2 ]
[ 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.
53%	at 80℃; Sealed tube	2-Difluoromethoxy-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine 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 NaHCO₃ and brine. The organic layer dried over MgSO₄, filtered and evaporated. Purification by flash chromatography on silica gel (CH2Cl2/MeOH, 95/5) gave the title compound (197 mg, 53percent yield). MS: 272.8 [M+H]⁺, Rt⁽⁶⁾=3.12 min.

Reference： [1] Patent: WO2013/57711, 2013, A1, . Location in patent: Page/Page column 49
[2] Patent: US2015/342951, 2015, A1, . Location in patent: Paragraph 0859-0860

[ 1054483-78-1 ] Synthesis Path-Downstream 1~1

1
[ 1054483-78-1 ]
[ 74-88-4 ]
[ 1002309-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In acetonitrile; at 50℃; for 16h;Sealed vial;	Step 2: l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2(lH)-one [00346] Iodomethane (0.283 mL, 4.52 mmol) was added to a mixture of 5-(4,4,5,5- tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2-ol (0.500 g, 2.262 mmol) and potassium carbonate (1.563 g, 11.31 mmol) in acetonitrile (10 mL). The reaction vial was sealed and stirred at 50 °C for 16 h. The resulting mixture was filtered to remove the inorganic salt and the filter cake rinsed with ethyl acetate. The filtrate was concentrated, treated with ethyl acetate (20 mL) and dichloromethane (20 mL), and filtered to remove the residual inorganic salt. The filtrate was concentrated and dried under vacuum to give crude l-methyl-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)pyridin-2(lH)-one as white solid (399.4 mg). This material was used in subsequent Suzuki coupling reactions without further purification. 1H NMR (400 MHz, chloroform-if) delta ppm 7.76 (d, J=2.0 Hz, 1H), 7.60 (dd, J=9.2, 2.0 Hz, 1H), 6.52 (d, J=9.0 Hz, 1H), 3.55 (s, 3H), 1.31 (s, 12H).

Reference： [1]Patent: WO2012/125893,2012,A1 .Location in patent: Page/Page column 212-213

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