[ CAS No. 62150-45-2 ] {[proInfo.proName]}

Name: 62150-45-2|4-Bromopyridine-2-carbonitrile|97%
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2D 3D

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Quality Control of [ 62150-45-2 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 62150-45-2 ]

Product Details of [ 62150-45-2 ]

CAS No. :	62150-45-2	MDL No. :	MFCD04065805
Formula :	C₆H₃BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	CZXDCTUSFIKLIJ-UHFFFAOYSA-N
M.W :	183.01	Pubchem ID :	693283
Synonyms :

Calculated chemistry of [ 62150-45-2 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	6
Fraction Csp3 :	0.0
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	36.65
TPSA :	36.68 Å²

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) :	-6.28 cm/s

Lipophilicity

Log Po/w (iLOGP) :	1.54
Log Po/w (XLOGP3) :	1.6
Log Po/w (WLOGP) :	1.72
Log Po/w (MLOGP) :	0.56
Log Po/w (SILICOS-IT) :	2.02
Consensus Log Po/w :	1.49

Druglikeness

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

Water Solubility

Log S (ESOL) :	-2.48
Solubility :	0.612 mg/ml ; 0.00334 mol/l
Class :	Soluble
Log S (Ali) :	-1.98
Solubility :	1.91 mg/ml ; 0.0104 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-2.96
Solubility :	0.199 mg/ml ; 0.00109 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.94

Safety of [ 62150-45-2 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P301+P312+P330	UN#:
Hazard Statements:	H302	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 62150-45-2 ]

* 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 [ 62150-45-2 ]
Downstream synthetic route of [ 62150-45-2 ]

[ 62150-45-2 ] Synthesis Path-Upstream 1~9

1
[ 14248-50-1 ]
[ 7677-24-9 ]
[ 62150-45-2 ]

Reference： [1] Inorganic Chemistry, 2015, vol. 54, # 21, p. 10483 - 10489
[2] Patent: US2009/239876, 2009, A1, . Location in patent: Page/Page column 24

2
[ 14248-50-1 ]
[ 62150-45-2 ]

Reference： [1] Patent: US5750520, 1998, A,

3
[ 1120-87-2 ]
[ 62150-45-2 ]

Reference： [1] Inorganic Chemistry, 2015, vol. 54, # 21, p. 10483 - 10489

4
[ 19524-06-2 ]
[ 62150-45-2 ]

Reference： [1] Patent: US2009/239876, 2009, A1,

5
[ 4248-19-5 ]
[ 62150-45-2 ]
[ 262295-94-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With palladium diacetate; caesium carbonate; XPhos In 1,4-dioxane at 100℃; for 1 h;	To a solution of 4-bromopyridine-2-carbonitrile (20 g, 109.29 mmol) in 1,4-dioxane (300 mL) was added Pd(OAc)₂ (2.98 g, 13.27 mmol), XPhos (18.9 g, 39.34), Cs₂CO₃ (50.3 g, 154.38 mmol). The resulting solution was stirred for 1 h at 100° C. The reaction was cooled to room temperature and the solids were removed by filtration. The filtrate was concentrated and the resulting residue was purified by flash column chromatography (EtOAc/petroleum ether=1/3 (v/v)) to provide the desired product as a yellow solid (23 g, 95percent). LC-MS (ES, m/z): 220 [M+H]⁺. ¹H NMR (300 MHz, CDCl₃): δ 8.49 (d, J=5.6 Hz, 1H), 7.87 (d, J=2.2 Hz, 1H), 7.43 (dd, J=5.6, 2.2 Hz, 1H), 6.90 (s, 1H), 1.54 (s, 9H) ppm.

Reference： [1] Patent: US2016/243100, 2016, A1, . Location in patent: Paragraph 0257-0258

6
[ 62150-45-2 ]
[ 284462-37-9 ]

Reference： [1] Patent: CN105801475, 2016, A,

7
[ 62150-45-2 ]
[ 1256785-86-0 ]

Reference： [1] Patent: US2016/243100, 2016, A1,

8
[ 62150-45-2 ]
[ 865156-48-5 ]

Reference： [1] Patent: WO2014/8197, 2014, A1,
[2] Patent: WO2015/95767, 2015, A1,

9
[ 62150-45-2 ]
[ 865156-50-9 ]

Reference： [1] Patent: WO2005/90305, 2005, A1, . Location in patent: Page/Page column 30
[2] Patent: WO2005/90304, 2005, A1, . Location in patent: Page/Page column 38-39
[3] Patent: WO2014/8197, 2014, A1, . Location in patent: Page/Page column 106

[ 62150-45-2 ] Synthesis Path-Downstream 1~88

1
[ 62150-45-2 ]
[ 269409-70-3 ]
[ 952742-96-0 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; ethanol; water; at 100℃;Microwave irradiation;	Preparation 10: 4-(4-Hydroxyphenyl)picolinonitrile <n="21"/>A mixture of <strong>[62150-45-2]4-bromo-2-cyanopyridine</strong> (2.05g, 11.21mmol), 4-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)phenol (2.47g, 11.21mmol), 3M Na2CO3 (3.74mL, 11.21mmol) and [l,r-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.82g, 1.12mmol) in 4:1, ethylene glycol dimethylether : ethanol (1OmL) was reacted in the microwave at 1000C. The progress of the reaction was monitored by LCMS. The reaction mixture was filtered through celite and the filtrate evaporated. The crude material was purified by flash chromatography, followed by trituration with diethyl ether to afford the title compound: RT = 2.07min; m/z (ES+) = 197.07 [M+H]+.

Reference： [1]Patent: WO2007/116230,2007,A1 .Location in patent: Page/Page column 19-20

2
[ 62150-45-2 ]
[ 1066-54-2 ]
[ 802905-85-7 ]

Yield	Reaction Conditions	Operation in experiment
41%	With triphenylphosphine;bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide; In tetrahydrofuran; at 20℃; for 73h;	4-Bromo-2-pyridinecarbonitrile [Cesko-Slovenska Farmacie 25(5), 181(1976)] (0.73 g, 4.0 mmol) was dissolved in 18 mL dry THF. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (31 mg, 0.12 mmol) and bis(triphenylphosphine)palladium(II) chloride (141 mg, 0.20 mmol) were added and the reaction mixture was stirred at room temperature for 1 h. Copper(I) iodide (23 mg, 0.12 mmol) and trimethylsilyl-acetylene (590 mg, 6.0 mmol) were added. The reaction mixture was stirred at room temperature for 3 days. The solvent was evaporated. The residue was taken up in 100 mL water and extracted three times with 100 ml of ethyl acetate. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/methylene chloride 1:2). The desired product was obtained as a yellow oil (329 mg, 41percent), MS: m/e=201.3 (M+H+).
41%	With triphenylphosphine;bis(triphenylphosphine)palladium(II)-chloride; copper(I) iodide; In tetrahydrofuran; water;	4-Trimethylsilanylethynyl-pyridine-2-carbonitrile 4-Bromo-2-pyridinecarbonitrile [Cesko-Slovenska Farmacie 25(5),181(1976)] (0.73 g, 4.0 mmol) was dissolved in 18 mL dry THF. This mixture was evacuated and backfilled with argon several times to remove oxygen from the solution. Triphenylphosphine (31 mg, 0.12 mmol) and bis(triphenylphosphine)palladium(II) chloride (141 mg, 0.20 mmol) were added and the reaction mixture was stirred at room temperature for 1 h. Copper(I) iodide (23 mg, 0.12 mmol) and trimethylsilyl-acetylene (590 mg, 6.0 mmol) were added. The reaction mixture was stirred at room temperature for 3 days. The solvent was evaporated. The residue was taken up in 100 mL water and extracted three times with 100 ml of ethyl acetate. The combined organic extracts were dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (heptane/methylene chloride 1:2). The desired product was obtained as a yellow oil (329 mg, 41percent), MS: m/e=201.3 (M+H+).

Reference： [1]Patent: US2004/248888,2004,A1 .Location in patent: Page 13
[2]Patent: US2005/143375,2005,A1

3
[ 62150-45-2 ]
[ 169250-16-2 ]
1-(4-bromo-pyridin-2-yl)-4-methoxy-butan-1-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		b) 1- (4-Bromo-pvridin-2-vl)-4-methoxv-butan-1-one; The Grignard reagent prepared from 20 mmol of 3-methoxypropylbromide and 22 mmol of magnesium in dry ether (100 mi) is added slowly to 30 mmol of <strong>[62150-45-2]4-bromo-2-cyanopyridine</strong> in 80 ml of dry ether under argon. The reactions mixture is stirred for 12 hours at room temperature and 5M HCI is added. The mixture is made alkaline with 25percent aqueous ammonium hydroxide solution and the layers are separated. The organic layer is dried over sodium sulphate and evaporated. Flash chromatography (Si02 60F) of the residue provides the title compound which is identified on the basis of the Rf value.

Reference： [1]Patent: WO2005/90305,2005,A1 .Location in patent: Page/Page column 32

4
ammonium chloride [ No CAS ]
[ 62150-45-2 ]
[ 108957-20-6 ]
[ 106-93-4 ]
[ 150971-76-9 ]

Yield	Reaction Conditions	Operation in experiment
	With chloro-trimethyl-silane; zinc;bis(triphenylphosphine)palladium(II)-chloride; In tetrahydrofuran; ethyl acetate; toluene;	PREPARATION 11 N-t-Butoxycarbonyl-3-(2-cyano-4-pyridyl)-(S)-alanine benzyl ester 1,2-Dibromoethane (13 mul, 0.14 mmol) was added, under dry nitrogen, to a stirred suspension of zinc dust (240 mg, 3.6 mmol) in anhydrous tetrahydrofuran (1 ml), then the resulting mixture gently heated until the first sign of boiling was evident and allowed to cool to room temperature; this process was repeated twice, after which trimethylsilyl chloride (15 mul, 0.11 mmol) was added and stirring continued for 15 minutes at room temperature. A solution of benzyl 2(R)-t-butoxycarbonylamino-3-iodopropionate (0.5 g, 1.2 mmol), obtained by the method described in J. Org. Chem., 1992, 57, 3397, in anhydrous tetrahydrofuran (2 ml) was next added over 1 minute. After a further 1.5 hours at room temperature, the reaction mixture was treated with bis(triphenylphosphine)palladium(II) chloride (75 mg, 0.1 mmol), followed by <strong>[62150-45-2]4-bromo-2-cyanopyridine</strong> (Preparation 10; 270 mg, 1.4 mmol), and stirred for 18 hours more at room temperature, before being treated with ethyl acetate (10 ml) and saturated aqueous ammonium chloride solution (5 ml) and then filtered. The organic phase was separated, washed successively with 1M aqueous citric acid solution, saturated aqueous sodium bicarbonate solution and saturated brine, dried (MgSO4) and evaporated under reduced pressure. The residue was purified by chromatography on silica gel, using an elution gradient of ethyl acetate:toluene (0:100 to 25:75), to afford the title compound (250 mg) as an oil which subsequently presented as a white foam, m.p. 74°-76° C. Rf 0.59 (SS 12). [alpha]D25 -24° (c=0.1, CH3 OH). Found: C,66.14; H,5.91; N,10.75. C21 H23 N3 O4 requires C,66.12; H 6.08; N,11.02percent.

Reference： [1]Patent: US5750520,1998,A

5
[ 62150-45-2 ]
[ 14202-12-1 ]
C₁₀H₁₃BrN₂O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In tetrahydrofuran; at 20℃; for 0.166667h;	A solution of 4.3 g of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> [62150-45-2] in 10 ml of tetrahydrofuran is added to a solution of 8.79 g of 3-methoxypropylmagnesium chloride [14202-12-1] in 10 ml of tetrahydrofuran. The reaction solution is stirred at room temperature for 10 minutes and then 50 ml of methanol are added. 2.7 g of sodium borohydride are added to the solution over the course of 30 minutes, and the mixture is stirred at room temperature for 2.5 hours. It is diluted with ethyl acetate and basified with 1 M sodium hydroxide solution. The phases are separated. The aqueous phase is extracted with ethyl acetate (2X). The combined organic phases are evaporated. The crude title compound is obtained as an orange oil from the residue. Rt = 2.47 (Gradient I).

Reference： [1]Patent: WO2007/31558,2007,A1 .Location in patent: Page/Page column 28

6
(4-((methoxycarbonyl) amino)phenyl)boronic acid [ No CAS ]
[ 62150-45-2 ]
[ 1035018-25-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 150℃; for 0.25h;Microwave irradiation;	7A. [4-(2-Aminomethyl-pyridin-4-yl)-phenyl]-carbamic acid methyl ester: 7e?ralpha.pound.:zchitriphenylphosphine)palladium (0) (0.063g, 0.055 mmol) was added to a degassed solution of DME/H2O (4: 1, 8 mL) containing, A- (methoxycarbonylamino)phenylboronic acid (0.32 g, 1.64 mmol) , A- bromopicolinonitrile (0.20 g, 1.09 mmol) and potassium carbonate (0.906 g, 6.56 mmol) under a blanket of argon. The mixture was irradiated at 150 0C microwave conditions for 15 min. The cooled solution was partitioned between EtOAc (20 mL) and H2O (20 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2 x 10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to leave a tan solid. The residue was dissolved 2.0 M N^/MeOH (20 mL) treated with a slurry of Raney Ni (in water) and stirred under a hydrogen atmosphere (50 psi) for 14 h. The suspension was filtered through a plug of Celite , the filter-cake was rinsed with MeOH and the combined filtrates were concentrated to give 7A as a tan solid. The crude product was carried forward to the next reaction without purification. LC/MS m/z 258 (M + H)+.

Reference： [1]Patent: WO2008/76805,2008,A2 .Location in patent: Page/Page column 124

7
[ 62150-45-2 ]
[ 1179360-58-7 ]

Yield	Reaction Conditions	Operation in experiment
74.8%		[00830] To a solution of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (1 g, 5.46 mmol) in anhydrous MeOH (4mL) was added sodium methoxide in MeOH (0.5 M, 2.19 mL, 1.1 mmol) and stirred at r.t. for 4h. To the reaction mixture was added ammonium chloride (0.32 g, 6 mmol) and stirred at r.t. overnight. The reaction was diluted with ether (10 mL) and stirred at r.t. for 30 mins. A precipitate formed that was collected by filtration, washed with ether (2 x 4mL) and dried under vacuum to afford the title compound (967mg, 74.8percent) as a white powder. [00831] Method B: LC-MS m/z = 199.8, 201.9 [M + H]+; RT = 0.2 min.
		To the product of Intermediate 2 (3.19 g, 17.43 mmol) in MeOH (11 mL) was added sodium methoxide (0.399 mL, 1.743 mmol, 25 wt percent in MeOH). The reaction was stirred at room temperature overnight when ammonium chloride (1.026 g, 19.17 mmol) was added. The reaction was refluxed for 2 h, cooled to room temperature and concentrated. The residue was suspended in anhydrous EtOH (100 mL), briefly refluxed and filtered. The filtrate stood at room temperature overnight and was concentrated to afford the title compound. HPLC/MS: 202.0 (M+1); Rt=0.35 min/202.1 (M+1); Rt=0.51 min.

Reference： [1]Patent: WO2017/59191,2017,A1 .Location in patent: Paragraph 00828-00831
[2]Patent: US2009/239876,2009,A1 .Location in patent: Page/Page column 24

8
[ 1038401-68-1 ]
[ 62150-45-2 ]
[ 865156-53-2 ]

Yield	Reaction Conditions	Operation in experiment
		b) 7-Methox-1,1,1-triphenyl-3-(4-bromopyridin-2-yl)-2-aza-1,No.5-phosphaheptane-1, 3-diene; 4. 62 g of (4-methoxybutyl)triphenylphosphonium iodide are taken up in 5 m (of anhydrous benzene under argon and 6. 3 mi of a methyllithium solution (1. 6M in diethyl ether) are added dropwise. The solution is heated to reflux and the resulting suspension is subsequently cooled to 0°C. A solution of 1. 83 g of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> [6215045-t in 4 ml of benzene is added and the reaction mixture is stirred at room temperature over 120 hours. Dichloromethane is added and the lithium salts are tittered off through Hyflo. The filtrate is concentrated. The title compound is identified on the basis of the Ru value from the residue by means of flash chromatography (lox)

Reference： [1]Patent: WO2005/90304,2005,A1 .Location in patent: Page/Page column 39

9
(4-((methoxycarbonyl) amino)phenyl)boronic acid [ No CAS ]
[ 62150-45-2 ]
[ 1035018-24-6 ]

Yield	Reaction Conditions	Operation in experiment
		7A. [4-(2-Aminomethyl-pyridin-4-yl)-phenyl]-carbamic acid methyl ester Tetrakis(triphenylphosphine)palladium (0) (0.063 g, 0.055 mmol) was added to a degassed solution of DME/H2O (4:1, 8 mL) containing, 4-(methoxycarbonylamino)phenylboronic acid (0.32 g, 1.64 mmol), <strong>[62150-45-2]4-bromopicolinonitrile</strong> (0.20 g, 1.09 mmol) and potassium carbonate (0.906 g, 6.56 mmol) under a blanket of argon. The mixture was irradiated at 150° C. microwave conditions for 15 min. The cooled solution was partitioned between EtOAc (20 mL) and H2O (20 mL). The layers were separated and the aqueous layer was extracted with EtOAc (2*10 mL). The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated to leave a tan solid. The residue was dissolved 2.0 M NH3/MeOH (20 mL) treated with a slurry of Raney Ni (in water) and stirred under a hydrogen atmosphere (50 psi) for 14 h. The suspension was filtered through a plug of Celite.(R)., the filter-cake was rinsed with MeOH and the combined filtrates were concentrated to give 7A as a tan solid. The crude product was carried forward to the next reaction without purification. LC/MS m/z 258 (M+H)+.

Reference： [1]Patent: US2010/16316,2010,A1 .Location in patent: Page/Page column 62

10
[ 62150-45-2 ]
[ 1357587-40-6 ]

Reference： [1]Patent: WO2012/16993,2012,A1

11
[ 62150-45-2 ]
[ 1357588-21-6 ]

Reference： [1]Patent: WO2012/16993,2012,A1

12
[ 1357588-07-8 ]
[ 62150-45-2 ]
[ 1357588-20-5 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 100℃; for 0.5h;Microwave irradiation; Inert atmosphere;	Method A, step c4-{4-(2-Cyano-pyridin-4-yl)-3-{3-[(2,5-difluoro-benzenesulfonyl)- methoxymethyl-amino]-2-fluoro-phenyl}-pyrazol-1-yl)-piperidine-1- carboxylic acid tert-butyl esterFormula 2, where R4 = 2-cyanopyridin-4-yl; PGi = methoxymethyl; R29 = N-ie/t-butoxycarbonyl-piperidin-4-yl; R30 - 2,5-difiuoro-benzene- sulfonyl[00317] In a microwave tube a solution of 4-[3-{3-[(2)5-difluoro- benzenesulfonyl)-methoxymethyl-amino]-2-fluoro-phenyl}-4-(414.5F5- tetramethyl-[1 ,3,2]dioxaborolan-2-yl)-pyrazol-1 -yl]-piperidine- 1 -carboxylic acid tert-butyl ester (0.708 mmol) {prepared as described in Example 13) in DME/H20 9:1 (10 mL) was degassed by bubbling argon for 5 minutes. 4- Bromo-2-cyano-pyridine (259 mg, 1.416 mmoi, 2 eq) was then added, followed by cesium carbonate (577 mg, 1.770 mmol, 2.5 eq) andPd{dppf)C1/2-CH2Cl2 (58 mg, 0.071 mmol, 0.1 eq). The mixture was irradiated in the microwave oven at 100°C for 30 minutes and then partitioned between ethyl acetate and saturated aqueous NaHC03- The two phases were separated and the organic layer was washed again with saturated aqueous NaHC03 and then with brine. The combined organic layers were dried over Na2S04 and evaporated to dryness. The crude product was purified by chromatography on silica gel (cyclohexane/ethylacetate 1:1) affording 425 mg of the title compound.. HPLC (254 nm): Rt: 7.62 min; 'H NMR (DMSO~d6) Shift 8.63 (s, 1 H), 8.56 (d, J = 4.9 Hz, 1 H), 7.76 (d, J = 1.1 Hz, 1 H), 7.68 - 7,44 (m, 4 H), 7.38 - 7.29 (m, 3 H), 5.03 (s, 2 H), 4.56 - 4.37 (m, 1 H), 4.15 - 4.04 (m, 2 H), 3.29 (s, 3 H), 3.05 - 2.88 (m, 2 H), 2 20 - 2.08 (m, J = 9.6 Hz, 2 H), 1.83 (dq, J = 4.2, 12.2 Hz, 2 H), 1.43 (s, 9 H); HR S (ESI) calcd for C33H34F3N605S [M+Hf 683.2258, found 683.2242.

Reference： [1]Patent: WO2012/16993,2012,A1 .Location in patent: Page/Page column 154-155

13
[ 1357588-17-0 ]
[ 62150-45-2 ]
[ 1357588-18-1 ]

Yield	Reaction Conditions	Operation in experiment
	With caesium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In 1,2-dimethoxyethane; water; at 100℃; for 0.5h;Microwave irradiation; Inert atmosphere;	Method A, step cN~{3-[4-(2-Cyano-pyridin-4-yl)-1-(tetrahydro-pyran-4-yl)-1H-pyrazol-3-yl]- 2-fluoro-phenyl}-2,5-difluoro-N-methoxymethyl-benzenesulfonamide Formula 2, where R4 = 2-cyanopyridin-4-yl; PGi = methoxymethyl; R29 - tetrahydro-pyran-4-yl; R30 = 2,5-difluoro-benzene-sulfonyl[00313] In a microwave tube a solution of 2,5-difluoro-N-{2-fluoro~3-[1- (tetrahydro-pyran-4-yi)-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H- pyrazol-3-yl]-phenyl}-N-methoxymethyl-benzenesulfonamide (420 mg, 0.691 mmol) in DME/H2O 9:1 (10 mL) was degassed by bubbling argon for 5 minutes. 4-Bromo-2-cyano-pyridine (252 mg, 1.383 mmol, 2 eq) was then added, followed by cesium carbonate (563 mg, 1.728 mmol, 2.5 eq) and Pd(dppf)Cl2-CH2C.2 (56 mg, 0.069 mmol, 0.1 eq). The mixture was irradiated in the microwave oven at 100°C for 30 minutes and then partitioned between ethyl acetate and saturated aqueous aHC03- the two phases were separated and the organic layer was washed again with saturated aqueous NaHCOs and then with brine. The combined organic layers were dried over Na2S04 and evaporated to dryness. The crude product was purified by chromatography on silica gel (gradient cyclohexane/ethyl acetate 1:1 to 1 :2) affording 210 mg of the title compound (52percent yield) as a white solid, HPLC (254 nm): Rt: 6,69 min; H NMR (DMSO-d6) Shift: 8.63 (s, 1 H), 8.56 (d, J = 5.4 Hz, 1 H), 7,76 (d, J = 1.1 Hz, 1 H), 7.70 - 7.45 (m, 4 H), 7,42 - 7.25 (m, 3 H), 5.03 (s, 2 H), 4.61 - 4.35 (m, 1 H), 4.04 - 3.96 {m, 2 H), 3.59 - 3.45 (m, 2 H), 3.26 (s, 3 H), 2.18 - 2.06 (m, 2 H), 2.05 - 1.93 (m, 2 H); HRMS (ESI) calcd for C28H25F3N504S [M+Hj+ 584.1574, found 584.1555.

Reference： [1]Patent: WO2012/16993,2012,A1 .Location in patent: Page/Page column 151-152

14
[ 62150-45-2 ]
[ 591-51-5 ]
[ 18714-16-4 ]

Reference： [1]Journal of the American Chemical Society,2012,vol. 134,p. 4533 - 4536
[2]Patent: WO2013/185021,2013,A2 .Location in patent: Paragraph 0049

15
[ 1431616-41-9 ]
[ 62150-45-2 ]
[ 1431616-38-4 ]

Reference： [1]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 514 - 516

16
[ 62150-45-2 ]
[ 123324-71-0 ]
[ 1431616-37-3 ]

Reference： [1]Journal of Materials Chemistry C,2019,vol. 7,p. 6592 - 6606
[2]ACS Medicinal Chemistry Letters,2013,vol. 4,p. 514 - 516

17
[ 62150-45-2 ]
[ 411235-57-9 ]
4-cyclopropylpyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
70%	With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In tetrahydrofuran; for 16h;Inert atmosphere; Reflux;	Step 1 : 4-Cyclopropylpicolinonitrile To a solution of <strong>[62150-45-2]4-bromopicolinonitrile</strong> (0.2 g, 1.1 mmol) in tetrahydrofuran were added cyclopropyl boronic acid (0.093 g, 1.1 mmol), and potassium phosphate tribasic (0.694 g, 3.2 mmol). The resulting reaction mixture was degassed with nitrogen for 10 minutes and then added Pd(OAc)2 and S-phos were added. The reaction mixture was heated at reflux for 16 h,then was diluted with water and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure and the residue was purified via flash chromatography (10percent ethyl acetate in petroleum ether) to afford 4- cyclopropylpicolinonitrile (0.1 g, 70percent). MS (ES+APCI) (M+H) 145.2; LCMS retention time 3.02 min (Method J).

Reference： [1]Patent: WO2013/150416,2013,A1 .Location in patent: Page/Page column 95

18
[ 62150-45-2 ]
ethyl 4-cyclopropylpicolinimidate [ No CAS ]

Reference： [1]Patent: WO2013/150416,2013,A1

19
[ 62150-45-2 ]
[ 865156-49-6 ]

Reference： [1]Patent: WO2014/8197,2014,A1
[2]Patent: WO2015/95767,2015,A1

20
[ 62150-45-2 ]
[ 1533440-89-9 ]

Reference： [1]Patent: WO2014/8197,2014,A1
[2]Patent: WO2015/95767,2015,A1

21
[ 75-16-1 ]
[ 62150-45-2 ]
[ 1270432-26-2 ]

Yield	Reaction Conditions	Operation in experiment
		Compound 66.1. l-(4-Bromopyridin-2-yl)ethanamine. Into a 500-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methylmagnesium bromide (3 M in THF) (63.4 mL, 190 mmol) in THF (100 mL). A solution of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (1 1.6 g, 63.4 mmol; patent US 2009/0239876 Al , example 2) in THF (40 mL) was added drop-wise at room temperature over 40 min. Methanol (40 mL) was then added drop-wise followed by portion- wise addition of sodium borohydride (1 1.8 g, 312 mmol) in several batches. The resulting mixture was stirred at room temperature for 2 h, then diluted with ethyl acetate (200 mL). The pH of the mixture was adjusted to 9 with aqueous sodium hydroxide (1 M) and the solids were removed by filtration. The filtrate was extracted with ethyl acetate (2 x 100 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to yield 10.3 g (crude) of the title compound as a yellow oil.
		Compound 66.1. l-(4-Bromopyridin-2-yl)ethanamine. Into a 500-mL 3-necked round-bottom flask, purged and maintained with an inert atmosphere of nitrogen, was placed a solution of methylmagnesium bromide (3 M in THF) (63.4 mL, 190 mmol) in THF (100 mL). A solution of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (1 1.6 g, 63.4 mmol; patent US 2009/0239876 Al, example 2) in THF (40 mL) was added drop-wise at room temperature over 40 min. Methanol (40 mL) was then added drop-wise followed by portion-wise addition of sodium borohydride (11.8 g, 312 mmol) in several batches. The resulting mixture was stirred at room temperature for 2 h, then diluted with ethyl acetate (200 mL). The pH of the mixture was adjusted to 9 with aqueous sodium hydroxide (1 M) and the solids were removed by filtration. The filtrate was extracted with ethyl acetate (2 x 100 mL) and the combined organic layers were dried over anhydrous sodium sulfate, filtered, and concentrated under reduced (crude) of the title compound as a yellow oil.

Reference： [1]Patent: WO2014/8197,2014,A1 .Location in patent: Page/Page column 137
[2]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 152

22
[ 62150-45-2 ]
[ 1583292-88-9 ]

Reference： [1]European Journal of Organic Chemistry,2014,vol. 2014,p. 436 - 441
[2]European Journal of Organic Chemistry,2014,vol. 2014,p. 436 - 441

23
6-(trifluoromethyl)-3-pyridinylboronic acid [ No CAS ]
[ 62150-45-2 ]
[ 1590398-02-9 ]

Yield	Reaction Conditions	Operation in experiment
66%	With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In N,N-dimethyl-formamide; at 120℃; for 14h;Inert atmosphere; Sealed tube;	A solution of 6-(trifluoromethyl)pyridine-3-ylboronic acid (1.04 g, 5.46 mmol), 4-bromo-pyridine-2- carbonitrile (1.00 g, 5.46 mmol) and potassium carbonate (0.76 g, 5.46 mmol) in DMF (5 mL) at 25°C was purged with nitrogen gas and evacuated three times. The solution was then treated with tetrakis(triphenylphosphine)palladium(0) (316 mg, 273 imol) and then sealed and heated to 120°C for 14 h. The reaction mixture was cooled to 25°C, unsealed and poured into water. The aqueous phase was extracted three times with ethyl acetate. The combined organic layers were washed with brine and dried over magnesium sulfate. Filtration followed by concentration in vacuo gave a brown solid. Flash chromatography (80/20 hexanes/ethyl acetate) afforded 6-trifluoromethyl- [3,4?]bipyridinyl-2?-carbonitrile (0.90 g, 66percent) as a white solid. MH+ = 249.9.

Reference： [1]Patent: WO2014/49047,2014,A1 .Location in patent: Page/Page column 86; 87

24
[ 62150-45-2 ]
[ 1590398-03-0 ]

Reference： [1]Patent: WO2014/49047,2014,A1

25
[ 62150-45-2 ]
[ 1590397-37-7 ]

Reference： [1]Patent: WO2014/49047,2014,A1

26
[ 1621526-49-5 ]
[ 62150-45-2 ]
[ 1621525-25-4 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium phosphate; copper(l) iodide; (R,R)-N,N'-dimethyl-1,2-diaminocyclohexane; In toluene; at 25 - 90℃;Inert atmosphere;	INTERMEDIATE 32 4-(3-Bromo-4-ffuoro- lH-pyrazol- 1 -yl)picolinonitrile 3-bromo-4-fluoro-lH-pyrazole (100 mg, 0.606 mmol), K3P04 (232 mg, 1.091 mmol), Oil (34.6 mg, 0.182 mmol) and (lR^-N^-dimethylcyclohexane-l^-diamine (43.1 mg, 0.303 mmol) were added successively to a solution of 4- bromopicolinonitrile (222 mg, 1.212 mmol) in toluene (3 mL) at 25 °C and the reaction was stirred at 90 °C under N2 overnight. After the mixture was filtered and washed with EtOAc(10 mL x 3), the filtrate was collected and removed in vacuo to give the crude product. This was purified by flash chromatography (ISCO Combiflash, 12 g, Biotage Si column, ~30 mL/min, 100percent hexanes 5 min, gradient to 100percent EtOAc in hexanes 15min) to afford 4-(3-bromo-4-fluoro-lH-pyrazol-l- yl)picolinonitrile. LCMS calc. = 268.97 (M+H); found = 268.86 (M+H)+.

Reference： [1]Patent: WO2014/120346,2014,A1 .Location in patent: Page/Page column 49-50

27
(7S)-7-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-5-[4-(trifluoromethyl)phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-4-one [ No CAS ]
[ 62150-45-2 ]
4-[(7S)-7-methyl-4-oxo-5-[4-(trifluoromethyl)phenyl]-6,7-dihydropyrazolo[1,5-a]pyrazin-3-yl]pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 150℃; for 0.166667h;Microwave irradiation;	Example 12 4-[(75)-7-Methyl-4-oxo-5-[4-(trifiuoromethyl)phenyl]-6,7-dihydropyrazolo[l,5- a]pyrazin-3-yl]pyridine-2-c Pd(PPli3)4 (42 mg, 0.036 mmol) was added to a stirred suspension of intermediate I-33a (250 mg, 0.593 mmol) and <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (162 mg, 0.884 mmol) in 1,4-dioxane (4 mL) and a sat. sol. of Na2C03 (2 mL). The mixture was stirred at 150 °C for 10 min under microwave irradiation. Then the mixture was diluted with H20 and extracted with DCM. The organic layer was dried (Na2S04), filtered and the solvent evaporated in vacuo. The crude product was purified by flash column chromatography (silica; EtOAc in DCM 0/100 to 50/50). The desired fractions were collected and evaporated in vacuo. The residue was precipitated with DIPE. The solid was filtered to yield compound 127 as a white solid. 1H NMR (500 MHz, CDC13) delta ppm 1.77 (d, J=6.4 Hz, 3 H) 4.05 (dd, J=12.9, 7.4 Hz, 1 H) 4.32 (dd, J=12.7, 4.0 Hz, 1 H) 4.79 - 4.88 (m, 1 H) 7.51 (br. d, J=8.4 Hz, 2 H) 7.74 (br. d, J=8.4 Hz, 2 H) 7.86 (s, 1 H) 7.92 (dd, J=5.2, 1.7 Hz, 1 H) 8.04 - 8.14 (m, 1 H) 8.67 (d, J=5.2 Hz, 1 H).

Reference： [1]Patent: WO2014/195311,2014,A1 .Location in patent: Page/Page column 114

28
[ 1527475-73-5 ]
[ 62150-45-2 ]
C₂₂H₂₈N₆O₂Si [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2015,vol. 58,p. 419 - 432

29
[ 64-18-6 ]
[ 62150-45-2 ]
(4-bromopyridin-2-yl)methanamine formate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Compound 39.1. (4-Bromopyridin-2-yl)methanamine. To a 1-L round-bottom flask, was placed a solution of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (10 g, 95percent, 51.9 mmol; patent US 2009/0239876 Al, example 2) in tetrahydrofuran (220 mL), then BH3-THF complex (1 M) (330 mL) was added drop-wise with stirring at room temperature. The resulting solution was stirred overnight at room temperature, then carefully quenched with formic acid (100 mL). The mixture was concentrated under reduced pressure to yield the title compound as the formate salt which was a light yellow solid and was used in the next step without further purification.

Reference： [1]Patent: WO2015/95767,2015,A1 .Location in patent: Page/Page column 121

30
[ 62150-45-2 ]
(E)-1-(4-bromopyridin-2-yl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one [ No CAS ]

Reference： [1]Organic and Biomolecular Chemistry,2015,vol. 13,p. 9418 - 9426

31
[ 62150-45-2 ]
(R)-1-(4-bromopyridin-2-yl)-3,3,3-trichloro-2-methylpropan-1-one [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2015,vol. 137,p. 9551 - 9554

32
[ 925-90-6 ]
[ 62150-45-2 ]
[ 1220127-06-9 ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9628 - 9631
[2]Journal of the American Chemical Society,2015,vol. 137,p. 9551 - 9554

33
(5-thiohexyl-(3,4-ethylenedioxyhiophen-2yl))trimethylstannane [ No CAS ]
[ 62150-45-2 ]
4-(5-thiohexyl-(3,4-ethylenedioxythiophen-2-yl))picolinonitrile [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10483 - 10489

34
[ 1120-87-2 ]
[ 62150-45-2 ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10483 - 10489

35
[ 62150-45-2 ]
1-(4-(5-thiohexyl-(3,4-ethylenedioxythiophen-2-yl))pyridine-2-yl)ethanone [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10483 - 10489

36
[ 62150-45-2 ]
4-(5-thiohexyl-(3,4-ethylenedioxythiophen-2-yl))-2-(3-(trifluoromethyl)-1H-pyrazol-5-yl)pyridine [ No CAS ]

Reference： [1]Inorganic Chemistry,2015,vol. 54,p. 10483 - 10489

37
[ 62150-45-2 ]
N-(1-(4-bromopyridin-2-yl)-2-methylpropyl)formamide [ No CAS ]

Reference： [1]Patent: WO2015/188369,2015,A1

38
[ 62150-45-2 ]
7-bromo-1-isopropylimidazo[1,5-a]pyridine [ No CAS ]

Reference： [1]Patent: WO2015/188369,2015,A1

39
[ 62150-45-2 ]
1-isopropylimidazo[1,5-a]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: WO2015/188369,2015,A1

40
[ 62150-45-2 ]
1-isopropyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-7-amine [ No CAS ]

Reference： [1]Patent: WO2015/188369,2015,A1

41
[ 62150-45-2 ]
9-ethyl-N-(1-isopropyl-5,6,7,8-tetrahydroimidazo[1,5-a]pyridin-7-yl)-8-(2-methylpyrimidin-5-yl)-9H-purin-6-amine [ No CAS ]

Reference： [1]Patent: WO2015/188369,2015,A1

42
[ 1068-55-9 ]
[ 62150-45-2 ]
1-(4-bromopyridin-2-yl)-2-methylpropan-1-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1: Preparation of l-(4-bromopyridin-2-yl)-2-methylpropan-l-amineTo a solution of <strong>[62150-45-2]4-bromopicolinonitrile</strong> (5.0 g, 27 mmol) in toluene (150 mL) was added isopropylmagnesium chloride (15 mL, 2 N solution in THF, 30 mmol) drop wise at 0°C. The resulting solution was stirred at 0°C for 1 h, after which MeOH (100 mL) was carefully added. The reaction mixture was then treated with sodium borohydride (1.5 g, 41 mmol) in several portions. The reaction mixture was then allowed to come to RT and was stirred for 3 h, after which it was quenched by the addition of water (50 mL). The aqueous solution was extracted with EtOAc (4 x 150 mL), and the combined organic layers were washed with brine, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated in vacuo, and the resulting residue was purified by flash column chromatography (silica gel, eluting with 0 - 6percent MeOH in DCM) to afford l-(4-bromopyridin-2-yl)-2- methylpropan-1 -amine. MS (ESI) Calc'd for (C9H14BrN2) [M+H]+, 229, 231; found, 229, 231.

Reference： [1]Patent: WO2015/188369,2015,A1 .Location in patent: Page/Page column 108

43
[ 62150-45-2 ]
[ 1256785-86-0 ]

Reference： [1]Patent: US2016/243100,2016,A1

44
[ 62150-45-2 ]
phenyl (2-acetylpyridin-4-yl)carbamate [ No CAS ]

Reference： [1]Patent: US2016/243100,2016,A1

45
[ 62150-45-2 ]
[ 284461-73-0 ]

Reference： [1]Patent: CN105801475,2016,A

46
[ 62150-45-2 ]
sorafenib tosylate [ No CAS ]

Reference： [1]Patent: CN105801475,2016,A

47
[ 62150-45-2 ]
C₁₂H₉ClN₂O₂ [ No CAS ]

Reference： [1]Patent: CN105801475,2016,A

48
[ 62150-45-2 ]
[ 284462-37-9 ]

Reference： [1]Patent: CN105801475,2016,A

49
[ 123-30-8 ]
[ 62150-45-2 ]
[ 1012058-77-3 ]

Yield	Reaction Conditions	Operation in experiment
2038 g	With sodium hydroxide; In tetrahydrofuran; water; for 5.5h;Reflux; Large scale;	(1) The 1830g4--bromo-2-cyano pyridine in 8L of tetrahydrofuran, a solution of sodium hydroxide was added 1150g (650g NaOH + 650ml water) aminophenol and 50percent; the reaction was heated at reflux for 6h; heating distilled tetrahydrofuran; 9L concentrate was added water, pH 5.5 was added concentrated hydrochloric acid, precipitated brown solid gradually, suction, blowing the filter cake after drying, to give a brown solid 2038g, namely the intermediate 1 (100percent purity by next reaction step).

Reference： [1]Patent: CN105801475,2016,A .Location in patent: Paragraph 0034; 0035

50
[ 4248-19-5 ]
[ 62150-45-2 ]
[ 262295-94-3 ]

Yield	Reaction Conditions	Operation in experiment
95%	With palladium diacetate; caesium carbonate; XPhos; In 1,4-dioxane; at 100℃; for 1h;	To a solution of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (20 g, 109.29 mmol) in 1,4-dioxane (300 mL) was added Pd(OAc)2 (2.98 g, 13.27 mmol), XPhos (18.9 g, 39.34), Cs2CO3 (50.3 g, 154.38 mmol). The resulting solution was stirred for 1 h at 100° C. The reaction was cooled to room temperature and the solids were removed by filtration. The filtrate was concentrated and the resulting residue was purified by flash column chromatography (EtOAc/petroleum ether=1/3 (v/v)) to provide the desired product as a yellow solid (23 g, 95percent). LC-MS (ES, m/z): 220 [M+H]+. 1H NMR (300 MHz, CDCl3): delta 8.49 (d, J=5.6 Hz, 1H), 7.87 (d, J=2.2 Hz, 1H), 7.43 (dd, J=5.6, 2.2 Hz, 1H), 6.90 (s, 1H), 1.54 (s, 9H) ppm.

Reference： [1]Patent: US2016/243100,2016,A1 .Location in patent: Paragraph 0257-0258

51
[ 4248-19-5 ]
[ 62150-45-2 ]
tert-butyl (2-acetylpyridin-4-yl)carbamate [ No CAS ]

Reference： [1]Patent: US2016/243100,2016,A1

52
2-((1-(tert-butoxycarbonyl)piperidin-4-yl)oxy)-2-oxoacetic acid [ No CAS ]
[ 62150-45-2 ]
tert-butyl 4-(2-cyanopyridin-4-yl)piperidine-1-carboxylate [ No CAS ]

Reference： [1]Journal of the American Chemical Society,2016,vol. 138,p. 13862 - 13865

53
[ 62150-45-2 ]
1-(4-bromopyridin-2-yl)-3,3,3-trichloro-2-methylpropan-1-one [ No CAS ]

Reference： [1]Chemical Communications,2016,vol. 52,p. 9628 - 9631

54
[ 62150-45-2 ]
2-(4-bromopyridin-2-yl)-3H,4H,5H,6H,7H-cyclopenta[d]pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2017/59191,2017,A1

55
[ 62150-45-2 ]
2-{4-[4-(trifluoromethyl)piperidine-1-carbonyl]pyridin-2-yl}-3H,4H,5H,6H,7H-cyclopenta[d]pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2017/59191,2017,A1

56
[ 62150-45-2 ]
4-[4-(trifluoromethyl)piperidine-1-carbonyl]pyridine-2-carbonitrile [ No CAS ]

Reference： [1]Patent: WO2017/59191,2017,A1

57
[ 62150-45-2 ]
2-{4-[4-(trifluoromethyl)piperidine-1-carbonyl]pyridin-2-yl}-3H,4H-thieno[3,2-d]pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2017/59191,2017,A1

58
[ 62150-45-2 ]
2-(4-[4-(trifluoromethyl)piperidin-1-yl]sulfonyl}pyridin-2-yl)-3H,4H,5H,6H,7H-cyclopenta[d]pyrimidin-4-one [ No CAS ]

Reference： [1]Patent: WO2017/59191,2017,A1

59
4-bromopyridine-2-carboximidamide [ No CAS ]
[ 62150-45-2 ]
[ 814-75-5 ]
4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium chloride; sodium methylate; potassium carbonate;	Step 1. 4-Bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine 4-Bromopyridine-2-carbonitrile (1.0 g, 5.5 mmol, Synthonix) in MeOH (10 mL) was treated with sodium methoxide (25 wt percent in MeOH, 0.095 mL, 0.47 mmol) and the reaction was stirred for 1 hour. Ammonium chloride (0.37 g, 6.9 mmol) was added and the reaction was stirred for 4 days. Solvent was then removed in vacuo. Water (4 mL) and EtOAc (6 mL) were added, the mixture was saturated with solid NaCl, and the mixture was stirred overnight. The solid product was isolated by filtration and dried at 40° C. under vacuum overnight. The product was used below without further purification. To 4-bromopyridine-2-carboximidamide (0.50 g, 2.5 mmol) in DMF (5 mL) was added K2CO3 (0.52 g, 3.7 mmol) and 3-bromo-2-butanone (0.24 mL, 3.2 mmol). The reaction was stirred for 4 days. The reaction mixture was partitioned between EtOAc and H2O. The aqueous layer was extracted with two further portions of EtOAc. The combined organic extracts were washed sequentially with water and saturated NaCl solution. The organic solution was dried over Na2SO4, filtered, and concentrated. The crude product was triturated with methyl tert-butyl ether (MTBE, 2 mL) and the solid product was isolated by filtration and dried under vacuum at 40° C. for 3 hours. Yield: 372 mg, 59percent. LCMS (M+H)+: 252.0/254.0.

Reference： [1]Patent: US2017/190689,2017,A1

60
[ 1171897-39-4 ]
4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium [ No CAS ]
[ 62150-45-2 ]
tert-butyl (2'-cyano-3,4'-bipyridin-5-yl)carbamate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1. tert-Butyl (2'-cyano-3,4'-bipyridin-5-yl)carbamate A degassed mixture of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (1.0 g, 5.5 mmol, Synthonix), tert-butyl [5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-3-yl]carbamate (1.7 g, 5.4 mmol, Small Molecules, Inc.), CsF (2 g, 20 mmol, Aldrich), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (0.38 g, 0.54 mmol) in 1,4-dioxane (10 mL) and water (3 mL) was heated to 120° C. for 70 minutes. Upon cooling to room temperature, EtOAc and water were added. The layers were shaken and separated, and the organic layer was washed twice with water, once with brine, dried over Na2SO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-80percent EtOAc in hexanes. Yield: 1.1 g, 68percent. 1H NMR (400 MHz, CDCl3) delta 8.81 (d, J=5.1 Hz, 1H), 8.63-8.59 (m, 2H), 8.53 (s, 1H), 7.94 (s, 1H), 7.76 (dd, J=5.0, 1.4 Hz, 1H), 7.23 (s, 1H), 1.55 (s, 9H); LCMS (M+H)+: 297.2.

Reference： [1]Patent: US2017/190689,2017,A1

61
[ 269410-08-4 ]
4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium [ No CAS ]
[ 62150-45-2 ]
[ 622-95-7 ]
4-[1-(4-chlorobenzyl)-1H-pyrazol-4-yl]pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate;	Step 1. 4-[1-(4-Chlorobenzyl)-1H-pyrazol-4-yl]pyridine-2-carbonitrile 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.60 g, 3.1 mmol, Aldrich) in DMF (16 mL) was treated with 1-(bromomethyl)-4-chlorobenzene (0.70 g, 3.4 mmol, Aldrich) and K2CO3 (1.3 g, 9.3 mmol). After stirring for 2 hours, the mixture was partitioned between water and EtOAc. The organic layer was washed with water, followed by brine, dried over Na2SO4, filtered, and concentrated. The crude product (0.90 g, 2.8 mmol) was combined with <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (0.45 g, 2.4 mmol, Synthonix), CsF (1 g, 6 mmol), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (0.15 g, 0.22 mmol, Aldrich) in 1,4-dioxane (6 mL, 70 mmol) and water (1 mL, 70 mmol). The mixture was degassed and heated to 100° C. for 10 minutes. Upon cooling to room temperature, the mixture was partitioned between water and EtOAc. The organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-70percent EtOAc in hexanes. Yield: 0.38 g, 44percent.

Reference： [1]Patent: US2017/190689,2017,A1

62
[ 916326-10-8 ]
4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium [ No CAS ]
[ 62150-45-2 ]
ethyl 2'-cyano-3,4'-bipyridine-5-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1. Ethyl 2'-cyano-3,4'-bipyridine-5-carboxylate A degassed mixture of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (1.0 g, 5.5 mmol, Synthonix), ethyl 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)nicotinate (1.5 g, 5.4 mmol, Frontier Scientific), CsF (2 g, 20 mmol), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (0.38 g, 0.54 mmol, Aldrich) in 1,4-dioxane (10 mL) and water (3 mL) was heated to 120° C. for 2 hours. Upon cooling to room temperature, EtOAc and H2O were added. The biphasic mixture was filtered. The organic layer was washed with H2O, followed by brine, dried over Na2SO4, filtered and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-100percent EtOAc/hexanes. The eluent was evaporated and the solid was dried at 40° C. overnight. Yield: 0.9 g, 66percent. LCMS (M+H)+: 254.1.

Reference： [1]Patent: US2017/190689,2017,A1

63
[ 916326-10-8 ]
[ 62150-45-2 ]
Methyl 2-[amino(imino)methyl]-3,4-bipyridine-5-carboxylate [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1

64
[ 62150-45-2 ]
[ 622-95-7 ]
4-[1-(4-Chlorobenzyl)-1H-pyrazol-4-yl]pyridine-2-carboximidamide [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1

65
[ 62150-45-2 ]
[ 96034-52-5 ]
4-bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1. 4-Bromo-2-(4,5-dimethyl-1H-imidazol-2-yl)pyridine 4-Bromopyridine-2-carbonitrile (1.37 g, 7.51 mmol) (Synthonix) was treated according to the procedure of Example 75, Step 1, using 3,3-dimethoxybutan-2-amine (prepared as in J. Med. Chem. 2005, 48(14), 4618-4627). When complete, the reaction was evaporated to dryness. 1.0 N NaOH was added and the solid product was isolated by filtration and washed with water. The solid was dried by azeotropic removal of water by repeated evaporation from toluene via rotary evaporation. Yield: 1.32 g, 70percent. LCMS (M+H)+: 251.9, 254.0.

Reference： [1]Patent: US2017/190689,2017,A1

66
1H-pyrazole-4-boronic acid [ No CAS ]
4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium [ No CAS ]
[ 96042-30-7 ]
[ 62150-45-2 ]
4-(1H-Pyrazol-4-yl)pyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1. 4-(1H-Pyrazol-4-yl)pyridine-2-carbonitrile A degassed mixture of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (3.3 g, 18 mmol, Synthonix), 1H-pyrazol-4-ylboronic acid (2.00 g, 17.9 mmol, Aldrich), CsF (8 g, 50 mmol), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (1.3 g, 1.8 mmol, Aldrich) in 1,4-dioxane (50 mL) and water (10 mL) was heated to 120° C. for 2 h 40 minutes, then cooled to room temperature. The organic layer was separated, and the aqueous layer was extracted with two further portions of EtOAc. The combined organic extracts were washed with water and brine, dried over Na2SO4, filtered, and concentrated. The product was purified by flash chromatography, eluting with a gradient from 0-10percent MeOH/DCM. Yield: 1.16 g, 38percent. LCMS (M+H)+: 171.0.

Reference： [1]Patent: US2017/190689,2017,A1

67
[ 445264-60-8 ]
4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium [ No CAS ]
[ 62150-45-2 ]
5-Methoxy-3,4'-bipyridine-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		Step 1. 5-Methoxy-3,4'-bipyridine-2-carbonitrile A degassed mixture of <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (1.0 g, 5.5 mmol, Synthonix), 3-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine (1.3 g, 5.4 mmol, Aldrich), CsF (2 g, 20 mmol), and 4-(di-tert-butylphosphino)-N,N-dimethylaniline-dichloropalladium (2:1) (0.38 g, 0.54 mmol) in 1,4-dioxane (10 mL) and water (3 mL) was heated to 120° C. for 2 hours. Upon cooling, ethyl acetate and water were added into the reaction mixture and the solid product was isolated by filtration and dried under vacuum at 40° C. to afford 0.84 g of product. The filtrate, which contained product, was washed with water, followed by brine, dried over Na2SO4, filtered, and concentrated to afford crude product which was purified by trituration with DCM overnight and filtered to afford an additional 0.12 g of product. Combined yield: 0.96 g, 84percent. LCMS (M+H)+: 212.1.

Reference： [1]Patent: US2017/190689,2017,A1

68
[ 62150-45-2 ]
N-[2-(5-Methoxy-3,4'-bipyridin-2'-yl)-4-methyl-1H-imidazol-5-yl]acetamide [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1

69
[ 62150-45-2 ]
tert-Butyl {2-[amino(imino)methyl]-3,4-bipyridin-5-yl}carbamate [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1

70
[ 62150-45-2 ]
tert-Butyl [2-(5-phenyl-1H-imidazol-2-yl)-3,4-bipyridin-5-yl]carbamate [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1

71
[ 62150-45-2 ]
4-bromo-2-(4,5-dimethyl-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)pyridine [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1
[2]Patent: US2017/190689,2017,A1

72
[ 62150-45-2 ]
5-Chloro-2'-(4,5-dimethyl-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-3,4-bipyridine [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1
[2]Patent: US2017/190689,2017,A1

73
[ 62150-45-2 ]
(3R)-1-[2'-(4,5-Dimethyl-1H-imidazol-2-yl)-3,4'-bipyridin-5-yl]pyrrolidin-3-ol [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1
[2]Patent: US2017/190689,2017,A1

74
[ 62150-45-2 ]
Ethyl 2'-(4,5-dimethyl-1-[2-(trimethylsilyl)ethoxy]methyl}-1H-imidazol-2-yl)-3,4-bipyridine-5-carboxylate [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1
[2]Patent: US2017/190689,2017,A1

75
[ 62150-45-2 ]
(2'-(4,5-Dimethyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazol-2-yl)-3,4'-bipyridin-5-yl)methanol [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1
[2]Patent: US2017/190689,2017,A1

76
[ 62150-45-2 ]
4-(1-Benzyl-1H-pyrazol-4-yl)pyridine-2-carbonitrile [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1

77
[ 62150-45-2 ]
4-(1-Benzyl-1H-pyrazol-4-yl)-2-(5-methyl-1H-imidazol-2-yl)pyridine [ No CAS ]

Reference： [1]Patent: US2017/190689,2017,A1

78
[ 55064-41-0 ]
[ 62150-45-2 ]
4-bromo-2-(4-methyl-1H-imidazol-2-yl)pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With 1,6-anhydro-2,2',3,3',4',6'-hexa-O-acetyl-beta-D-lactose; hydrogenchloride; sodium methylate; potassium carbonate;	Step 1. 4-Bromo-2-(4-methyl-1H-imidazol-2-yl)pyridine To <strong>[62150-45-2]4-bromopyridine-2-carbonitrile</strong> (0.500 g, 2.73 mmol, Synthonix) in MeOH (3 mL) was added sodium methoxide (25 wt percent in MeOH, 0.050 mL, 0.24 mmol, Aldrich) and the reaction mixture was heated at 40° C. for 1 hour. Upon cooling to room temperature, 1,1-diethoxypropan-2-amine (0.40 g, 2.7 mmol, AstaTech) and AcOH (0.3 mL) were added. The reaction mixture was heated in an oil bath held at 100° C. for 30 minutes. The reaction mixture was removed from the bath, MeOH (1.5 mL) and 6 N HCl (1.25 mL, 7.50 mmol) were added, and heating was resumed at 70° C. for 5 hours. Upon cooling to room temperature, solvent was removed via rotary evaporation. Potassium carbonate in water was added to adjust the pH to 10 and the precipitated product was stirred for 1 hour and isolated by filtration and air dried. Yield: 0.57 g, 88percent. 1H NMR (400 MHz, d6-DMSO) delta 12.65 (br s, 1H), 8.45 (d, J=5.3 Hz, 1H), 8.11 (d, J=1.6 Hz, 1H), 7.58 (dd, J=5.3, 1.9 Hz, 1H), 6.88 (s, 1H), 2.21 (s, 3H); LCMS (M+H)+: 238.0/240.0.

Reference： [1]Patent: US2017/190689,2017,A1

79
[ 62150-45-2 ]
C₆H₆BrN₃O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
97%	With hydroxylamine hydrochloride; potassium carbonate; In ethanol; water; at 80℃; for 12h;	Example 14A: To a solution of <strong>[62150-45-2]4-bromo-2-pyridinecarbonitrile</strong> ([62150-45-2], 1.75 g, 9.56 mmol, 1 eq) in a mixture of ethanol (25 mL) and H20 (25 mL) was added hydroxylamine hydrochloride (1.66 g, 24 mmol, 2.50 eq) and K2C03 (2 eq) at 20°C. The reaction was stirred at 80 °C for 12 hours. The reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate (30 mL) and washed with H20 (30 mL*2). The organic layer was dried over sodium sulfate and concentrated in vacuo to give the target compound (2.00 g, 9.26 mmol, 97percent yield) as a white solid. NMR (400 MHz, CDC13) delta 8.38 (d, J=5.3 Hz, 1H), 8.13 (d, J=1.8 Hz, 1H), 7.48 (dd, J=1.8, 5.3 Hz, 1H).

Reference： [1]Patent: WO2017/143011,2017,A1 .Location in patent: Paragraph 0196-0198

80
[ 62150-45-2 ]
C₁₁H₁₀BrN₃O₂ [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

81
[ 62150-45-2 ]
C₁₉H₁₇BrClN₃O₂ [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

82
[ 62150-45-2 ]
C₁₇H₁₃BrClN₃O₂ [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

83
[ 62150-45-2 ]
C₁₇H₁₅BrClN₃O [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

84
[ 62150-45-2 ]
C₁₉H₁₈ClN₃O₃ [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

85
[ 62150-45-2 ]
C₁₈H₁₆ClN₃O₃ [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

86
[ 62150-45-2 ]
C₁₈H₁₆BrClN₄O [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

87
[ 62150-45-2 ]
C₂₀H₁₉ClN₄O₃ [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

88
[ 62150-45-2 ]
C₁₉H₁₇ClN₄O₃ [ No CAS ]

Reference： [1]Patent: WO2017/143011,2017,A1

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Precautionary Statements-General
Code	Phrase
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Prevention
Code	Phrase
P201	Obtain special instructions before use.
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P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
P241	Use explosion-proof electrical/ventilating/lighting/equipment.
P242	Use only non-sparking tools.
P243	Take precautionary measures against static discharge.
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P262	Do not get in eyes, on skin, or on clothing.
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P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
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P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
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P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
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P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
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P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
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

[ CAS No. 62150-45-2 ] {[proInfo.proName]}

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[ 62150-45-2 ] Synthesis Path-Upstream 1~9

[ 62150-45-2 ] Synthesis Path-Downstream 1~88

Similar Product of [ 62150-45-2 ]

Related Functional Groups of [ 62150-45-2 ]

Bromides

Nitriles

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Pyridines

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[ 62150-45-2 ]

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