[ CAS No. 153034-86-7 ] {[proInfo.proName]}

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2D 3D

Structure of 153034-86-7 * Storage: {[proInfo.prStorage]}

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Quality Control of [ 153034-86-7 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 153034-86-7 ]

SDS Specification

Alternatived Products of [ 153034-86-7 ]

Product Details of [ 153034-86-7 ]

CAS No. :	153034-86-7	MDL No. :	MFCD01861983
Formula :	C₅H₃ClIN	Boiling Point :	No data available
Linear Structure Formula :	-	InChI Key :	KJKIPRQNFDUULB-UHFFFAOYSA-N
M.W :	239.44	Pubchem ID :	1516511
Synonyms :

Calculated chemistry of [ 153034-86-7 ] Expand+

Physicochemical Properties

Num. heavy atoms :	8
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	1.0
Num. H-bond donors :	0.0
Molar Refractivity :	41.96
TPSA :	12.89 ?2

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.01 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.88
Log Po/w (XLOGP3) :	2.46
Log Po/w (WLOGP) :	2.34
Log Po/w (MLOGP) :	2.01
Log Po/w (SILICOS-IT) :	3.05
Consensus Log Po/w :	2.35

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	1.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-3.43
Solubility :	0.0891 mg/ml ; 0.000372 mol/l
Class :	Soluble
Log S (Ali) :	-2.37
Solubility :	1.01 mg/ml ; 0.00422 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.6
Solubility :	0.0606 mg/ml ; 0.000253 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	2.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.97

Safety of [ 153034-86-7 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P280-P305+P351+P338-P310	UN#:
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 153034-86-7 ]

* 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 [ 153034-86-7 ]
Downstream synthetic route of [ 153034-86-7 ]

[ 153034-86-7 ] Synthesis Path-Upstream 1~1

1
[ 153034-86-7 ]
[ 945717-09-9 ]

Reference： [1] Journal of Medicinal Chemistry, 2012, vol. 55, # 11, p. 5270 - 5290
[2] Chemical Communications, 2013, vol. 49, # 20, p. 2037 - 2039
[3] Patent: WO2017/117708, 2017, A1,

[ 153034-86-7 ] Synthesis Path-Downstream 1~12

1
[ 153034-86-7 ]
[ 30413-58-2 ]
[ 656800-41-8 ]

Yield	Reaction Conditions	Operation in experiment
86.4%	With copper(l) iodide; N,N,N,N,-tetramethylethylenediamine;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 60℃; for 4h;	To a solution of intermediate 1 (1.85g, 7. [74MMOL)] in dry THF (40m L) were added under nitrogen, TMEDA (20mL) and intermediate 3 (1. [1EQ, 1G,] 8. 51mmol). The resulting mixture was degassed with nitrogen for 10 min, then tetrakis [(TRIPHENLYPHOSPHINE) PALLADIUM (0)] (0. [464MOL,] 537mg) and copper iodide (0.928 mmol, 177mg) were added. The resulting mixture was heated at [60C] for 4h. The mixture was poured into a saturated solution of NH4CI and extracted with EtOAc. The organic phase was dried over [NA2SO4] and filtered. Solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel [(CH2CI2/ETOAC] 90: 10) to afford the title compound as a beige solid (1. 54g, 86.4%) ; ['H] NMR (300 MHz, [CDCL3) No. ]: 8. 29 (d, 1H), 7.52 (t, 1H), 7.39 (s, 1H), 7.34-7. 24 (m, 2H), 7.10 (d, 1 H), 2.50 (s, 3H).
86.4%	With N,N,N,N,-tetramethylethylenediamine;copper(l) iodide; tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 60℃; for 4h;	To a solution of intermediate 1 (1.85g, 7. [74MMOL)] in dry THF [(40ML)] were added under nitrogen TMEDA (20mL) and intermediate 3 (1. 1eq, 1g, 8. 51mmol). The resulting mixture was degassed with nitrogen for ten mins, tetrakis (triphenlyphosphine) palladium (0) (0.537g, 0. [464MOL)] and copper iodide (0. [177G,] 0.928 [MMOL)] were added and the mixture was heated at [60C] for 4hours. The mixture was poured into a saturated solution of NH4CI and extracted with EtOAc. The organic phase was dried over Na2SO4 and filtered. The solvent was removed under reduced pressure and the residue was purified by chromatography on silica gel (CH2CI2/EtOAc 90: 10) to afford the title compound as a beige solid (1.54g, 86.4%) [;'H] NMR (300 MHz, [CDCI3)] [8] ppm: 8.29 (d, 1H), 7.52 (t, 1H), 7.39 (s, 1H), 7.34-7. 24 (m, 2H), 7.10 (d, 1H), 2.50 (s, 3H).

Reference： [1]Patent: WO2004/13125,2004,A1 .Location in patent: Page 19-20
[2]Patent: WO2004/13135,2004,A1 .Location in patent: Page 43-44

2
[ 153034-86-7 ]
[ 98-80-6 ]
[ 42260-39-9 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium carbonate;dichloro[di-tert-butyl(chloro)phosphine]palladium(II) dimer; In methanol; for 3.00833h;	Example 1; 4-Aminomethyl-cyclohexanecarboxylic acid [2-phenyl-1-(4-phenyl-pyridin-2-yl)- ethyl] -amide, bistrifluoroacetic acid salt; [00335] lA. 2-Chloro-4-phenylpyridine: A flask was charged with 2-chloro- 4-iodo pyridine (2.5g, 10.4 mmol), phenylboronic acid (1.33 g, 10.96 mmol) , K2C03 (4.54 g, 32.88 mmol), PXPd2 (0.186 g, 0.261 mmol), and methanol (34.8 mL). Argon was blown through flask for 30 sec. The dark brown suspension was stirred for 3 h and then filtered, washing with methanol. The filtrate was concentrated to give 2.15 g as a brown solid. Column chromatography (120g silica gel column; gradient elution; 0-35% ethyl acetate/hexane) afforded lA (1.79 g, 90%) as a yellow solid. iH-NMR (400 MHz, CDCI3) 8: 8.43 (d, J = 5.3 Hz, 1H), 7.61 (dd, J = 8.2, 1.5 Hz, 2H), 7.54 (d, J = 2.2 Hz, 1H), 7.52-7.47 (m, 3H), 7.43 (dd, J = 5.1, 1.5 Hz, 1H). 13C-NMR (125 MHz, CDC13) No.: 152.2, 151.5, 149.9, 136.8, 129.6,129.2, 127.0, 122.0,120.4. MS 190.0 (M+H) + and 192.0 (M+2+H)+.
84%	With potassium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In tetrahydrofuran; water; for 2h;Inert atmosphere; Reflux;	To a mixture of 1 (57.36 g, 0.24 mol) in THF/H2O (400 mL/100 mL) were added phenylboric acid (24.2 g, 0.2 mol) and K2CO3 (82.8 g, 0.6 mol). PdCl2(dppf) (2 g) was then added after being charged with N2 three times. The resulting mixture was refluxed for 2 hrs, cooled, and partitioned between a.q. NH4C1 and EtOAc. The aqueous layer was washed with EtOAc. The combined organic layers were washed with water, brine and dried over Na2 S O4. The solvent was removed in vacuo and the residue was purified by silica gel column (PE:EA=10: 1) to afford 32 g of 2 (yield 84%).
82%	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,2-dimethoxyethane; water;Inert atmosphere; Reflux;	A mixture of 2-chloro-4-iodopyridine (20.0 g, 82 mmol), phenylboronicacid (10.2 g, 82 mmol), Pd(Ph3P)4 (2.84 g 2.46 mmol), sodium carbonate (26.0 g, 246 mmol), DME (600 mL) andwater (150 mL) was degassed with nitrogen and then refluxed overnight. The reaction was concentrated and the extractedwith ethyl acetate. The ethyl acetate layer was dried on Na2SO4 and then vacuum distilled to give 2-chloro-4-phenylpyridine(2.79 g, 12.7 mmol, 82 % yield).

51%

With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; toluene; for 12h;Inert atmosphere; Reflux;

To a 1 L three-necked flask were added 2-chloro-4-iodopyridine (50 g, 208.8 mmol), phenyl boronic acid (28 g, 229.7 mmol), Pd(PPh3)4 (12 g, 10.4 mmol), potassium carbonate (86 g, 626 mmol), toluene (500 mL) and water (200 mL), and then the resulting reaction mixture was heated to reflux for 12 h under N2 protection. Then the reaction solution was cooled to room temperature, separated, the organic phase was collected, the water phase was extracted with EA for several times, and the organic phase was combined, dried with MgSO4 and evaporated to dryness, purified via silica gel column chromatography, eluting with EA:PE=1:50 (v:v), to afford intermediate 1 (20 g, 51% yield) as a white solid.

Reference： [1]Inorganic Chemistry,2017,vol. 56,p. 8244 - 8256
[2]Patent: WO2005/123680,2005,A1 .Location in patent: Page/Page column 76
[3]Patent: WO2010/94242,2010,A1 .Location in patent: Preparation III.1
[4]Patent: EP2730583,2014,A1 .Location in patent: Paragraph 0229; 0230
[5]Patent: US2019/225635,2019,A1 .Location in patent: Paragraph 0132; 0133

3
[ 153034-86-7 ]
[ 780-69-8 ]
[ 42260-39-9 ]
[ 53344-74-4 ]

Reference： [1]Organic Letters,2013,vol. 15,p. 5378 - 5381

4
[ 153034-86-7 ]
[ 4406-77-3 ]
[ 42260-39-9 ]

Reference： [1]Organic Letters,2014,vol. 16,p. 1264 - 1267

5
[ 153034-86-7 ]
[ 603-33-8 ]
[ 42260-39-9 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium phosphate; palladium diacetate; triphenylphosphine; In N,N-dimethyl-formamide; at 90℃; for 1h;Inert atmosphere; Schlenk technique;	General procedure: An oven dried Schlenk tube was purged with nitrogen and charged with 3-iodopyridine (0.875 mmol, 179.3 mg), BiPh3 (0.25 mmol, 110 mg), K3PO4 (1.5 mmol, 318 mg), Pd(OAc)2 (0.025 mmol, 5.6 mg), PPh3 (0.1 mmol, 26.2 mg) followed by dry DMF (3 mL) under nitrogen atmosphere. The reaction mixture was stirred in an oil bath at 90°C for 1h. It was brought to rt, treated with water (10mL), and extracted with ethyl acetate (2×20 mL). The organic extract was treated with brine, dried over anhydrous MgSO4, and concentrated using rotary evaporator under the reduced pressure. The crude was subjected to silica gel column chromatography (5percent EtOAc/Hexane) to obtain 3-phenylpyridine (1.1) as colorless oil (115 mg, 98percent).

Reference： [1]Tetrahedron,2015,vol. 71,p. 338 - 349

6
[ 153034-86-7 ]
[ 75061-73-3 ]
[ 42260-39-9 ]

Reference： [1]Chemical Communications,2015,vol. 51,p. 4009 - 4012

7
[ 153034-86-7 ]
[ 885693-20-9 ]
tert-butyl 2'-chloro-5,6-dihydro-[3,4'-bipyridine]-1(2H)-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 70℃; for 16h;Sealed tube; Inert atmosphere;	A deoxygenated mixture of tert-butyl 3-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan- 2-yl)-5,6-dihydropyridine-l(2H)-carboxylate (110 mg, 0.356 mmol), 2-chloro-4-iodopyridine (102 mg, 0.427 mmol), 1 , l'-bis(di-tert-butylphosphino)ferrocene palladium dichloride (23.2 mg, 0.036 mmol), and cesium carbonate (232 mg, 0.711 mmol) in dioxane (1.62 mL) and water (0.162 mL) was heated at 70 °C in a sealed vessel for 16 h. The mixture was cooled to room termperature and partitioned between water and ethyl acetate (2x). The combined organic layers were washed with saturated aqueous sodium chloride, dried over sodium sulfate, and concentrated. The residue was purified by silica gel chromatography eluting with a gradient of hexanes:ethyl acetate - 95:5 to 35:65 to give the title compound. MS: mlz = 295.2 [M+l]+.

Reference： [1]Patent: WO2015/161014,2015,A1 .Location in patent: Page/Page column 86

8
[ 153034-86-7 ]
[ 841-76-9 ]
[ 42260-39-9 ]

Reference： [1]Journal of Organic Chemistry,2016,vol. 81,p. 787 - 802

9
[ 153034-86-7 ]
(x)C₄H₈O*C₁₈H₁₅In [ No CAS ]
[ 42260-39-9 ]

Reference： [1]Angewandte Chemie - International Edition,2014,vol. 53,p. 11620 - 11624
Angew. Chem.,2015,vol. 127,p. 11620 - 11624,5

10
[ 153034-86-7 ]
[ 871836-51-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2017,vol. 27,p. 4370 - 4376

11
[ 153034-86-7 ]
[ 197223-39-5 ]
2-chloro-4-(3,5-di-tert-butylphenyl)pyridine [ No CAS ]

Reference： [1]Journal of Materials Chemistry C,2018,vol. 6,p. 6385 - 6397

12
[ 153034-86-7 ]
[ 129488-10-4 ]
C₁₂H₉ClN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
47.3%	With palladium diacetate; caesium carbonate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In toluene; at 90℃;Inert atmosphere;	Compound TDI01117-1 (500 mg, 2.15 mmol) and 2-chloro-4-iodopyridine (615 mg, 2.58 mmol) were dissolvedin toluene (20 mL), palladium acetate (24.1 mg, 0.11 mmol), BINAP (137 mg, 0.22 mmol) and cesium carbonate (1.40g, 4.30 mmol) were added, purge with argon was performed for 3 times, and the reaction was performed in an oil bathat 90°C overnight. Thin layer chromatography (petroleum ether : ethyl acetate=1:1) indicated the reaction was complete.The reaction solution was cooled to room temperature, and filtered. The filtrate was concentrated under reduced pressure,and the crude product was purified by column chromatography (petroleum ether : ethyl acetate= 10:1 to 1:1) to affordcompound TDI01117-2 (350 mg, yellow solid, yield: 47.3percent).1H NMR (400 MHz, DMSO-d6) delta 13.09 (s, 1H), 9.00 (s, 1H), 8.05 (s, 1H), 7.93 (d, J = 6.0 Hz, 1H), 7.59 - 7.58 (m, 2H),7.23 -7.18 (m, 1H), 6.75 (dd, J = 6.0, 2.0 Hz, 1H), 6.70 (d, J = 1.6 Hz, 1H).

Reference： [1]Patent: EP3421465,2019,A1 .Location in patent: Paragraph 0177; 0178

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Isomers

Technical Information

? Alkyl Halide Occurrence ? General Reactivity ? Grignard Reaction ? Hiyama Cross-Coupling Reaction ? Kinetics of Alkyl Halides ? Kumada Cross-Coupling Reaction ? Preparation of Amines ? Reactions of Alkyl Halides with Reducing Metals ? Reactions of Amines ? Reactions of Dihalides ? Stille Coupling ? Substitution and Elimination Reactions of Alkyl Halides ? Suzuki Coupling

Historical Records

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[ 153034-86-7 ]

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H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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[ CAS No. 153034-86-7 ] {[proInfo.proName]}

Quality Control of [ 153034-86-7 ]

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Product Details of [ 153034-86-7 ]

Calculated chemistry of [ 153034-86-7 ] Expand+

Physicochemical Properties

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Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 153034-86-7 ]

Application In Synthesis of [ 153034-86-7 ]

[ 153034-86-7 ] Synthesis Path-Upstream 1~1

[ 153034-86-7 ] Synthesis Path-Downstream 1~12

Technical Information

Related Functional Groups of [ 153034-86-7 ]

Chlorides

Related Parent Nucleus of [ 153034-86-7 ]

Pyridines

Precautionary Statements-General

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Response

Storage

Disposal

Physical hazards

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[ 153034-86-7 ]

Related Parent Nucleus of
[ 153034-86-7 ]