Name: 944276-67-9|4-Bromo-2-iodobenzonitrile|95%
Brand: Ambeed
SKU: A823564
Price: 34.0 USD
Availability: InStock
Rating: 97 (30 reviews)

1
[ 623-00-7 ]
[ 944276-67-9 ]
[ 1006715-27-0 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 4-bromobenzenecarbonitrile In tetrahydrofuran; hexane; pentane at -30℃; for 2h; Stage #2: With iodine In tetrahydrofuran; hexane; pentane at 20℃; for 1h; Further stages.;

Reference： [1]Uchiyama, Masanobu; Kobayashi, Yuri; Furuyama, Taniyuki; Nakamura, Shinji; Kajihara, Yumiko; Miyoshi, Tomoko; Sakamoto, Takao; Kondo, Yoshinori; Morokuma, Keiji [Journal of the American Chemical Society, 2008, vol. 130, # 2, p. 472 - 480]

2
[ 944276-67-9 ]
2-butyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-1,3-diazaspiro[4.4]non-1-en-4-one [ No CAS ]
5-bromo-4'-((2-butyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium phosphate In ethanol; water; toluene at 120℃; for 0.5h; Inert atmosphere; Sealed tube; Microwave irradiation;	109 Intermediate 109a: 5-bromo-4'-((2-butyl-4-oxo-l,3-diazaspiro[4.4]non-l-en-3- yl)methyl)- [1 ,1 ' -biphenyl] -2-carbonitrile To a microwave vial containing PdCl2(dppf) (0.196 g, 0.268 mmol), Intermediate 033a (1.00 g, 2.44 mmol) and 4-bromo-2-iodobenzonitrile (0.975 g, 3.17 mmol) was added toluene (9.75 ml) followed by ethanol (2.44 ml) and K3PO4 (2 M, aq.) (2.44 ml, 4.87 mmol). N2 was sparged through the reaction mixture for 5 min before the vial was sealed and heated at 120 °C in the microwave for 30 min. The reaction mixture was diluted with EtOAc and washed with saturated aqueous NaHCO3. The organic phase was concentrated and purified by ISCO (0-100% EtOAc in hexanes) to afford Intermediate 109a (0.906 g, 1.95 mmol, 80 % yield) as a white solid. LC-MS (Method A2) RT = 0.87 min, MS (ESI) m/z: 464.6 (M+H)+. 1H NMR (400 MHz, CDCl3) δ 7.70 - 7.68 (m, 1H), 7.65 - 7.61 (m, 2H), 7.55 (d, 7=8.4 Hz, 2H), 7.31 (d, J=8.4 Hz, 2H), 4.77 (s, 2H), 2.40 - 2.32 (m, 2H), 2.02 (br d, J=4.6 Hz, 6H), 1.86 (br s, 2H), 1.67 - 1.58 (m, 2H), 1.44 - 1.31 (m, 2H), 0.90 (t, 7=7.4 Hz, 3H).

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1 Location in patent: Page/Page column 189

3
[ 944276-67-9 ]
[ 59016-93-2 ]
5-bromo-4'-(hydroxymethyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
60%	With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate In tetrahydrofuran; methanol at 120℃; for 1h; Microwave irradiation; Sealed tube;	Common Intermediate 1-001: 5-bromo-4'-(hydroxymethyl)-[l,l'-biphenyl]-2- carbonitrile To a solution of (4-(hydroxymethyl)phenyl)boronic acid (400 mg, 2.6 mmol), 4-bromo-2- iodobenzonitrile (800 mg, 2.6 mmol) and Pd(PPh3)4 (66 mg, 0.057 mmol) in THF/MeOH (3 : 1, 12 ml) was added 1.5 N Na2CC>3 (2.6 ml, 3.9 mmol). The reaction mixture was sealed, placed in a microwave reactor and heated at 120 °C for 60 min. LC-MS indicated completion of reaction. The reaction mixture was diluted with EtOAc/H20. The organic layer was collected, washed with brine, dried over Na2S04 and concentrated. The crude product was purified by flash chromatography (2% to 60% EtOAc in hexane over 18 min using a 40 g silica gel cartridge). The desired fractions were combined and concentrated to yield 1-001 (446 mg, 1.5 mmol, 60 % yield) as a white solid. H NMR (500 MHz, CDC13) δ 7.72 (d, 7=1.4 Hz, 1H), 7.67 - 7.60 (m, 2H), 7.60 - 7.51 (m, 4H), 4.81 (d, 7=5.5 Hz, 2H), 1.80 (br t, 7=5.8 Hz, 1H). 13C NMR (126 MHz, MeOH-i δ 148.4, 144.1, 137.1, 136.2, 134.5, 132.3, 130.0, 129.3, 128.5, 119.3, 65.1. LC-MS: Waters Aquity BEH C18 2.1x50 mm, 1.7m; A: 90% H20 + 0.05% TFA; B: 90% ACN + 0.05% TFA; wavelength 220 nm; flow rate 0.8 mL/min; gradient time 1.0 min; 2 to 98% B. RT = 0.86 min, MS (ESI) m/z: 270.0 and 272.0 (M-18)+.

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1 Location in patent: Page/Page column 86-87

4
[ 944276-67-9 ]
5-bromo-4'-((3,5-dimethyl-1H-1,2,4-triazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 3.5 h / 20 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

5
[ 944276-67-9 ]
5-(5,5-dimethyl-1,3,2-dioxaborinan-2-yl)-4'-((3,5-dimethyl-1H-1,2,4-triazol-1-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 3.5 h / 20 °C 4.1: potassium acetate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / 1,4-dioxane / 2.75 h / 85 °C / Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

6
[ 944276-67-9 ]
4'-((3,5-dimethyl-1H-1,2,4-triazol-1-yl)methyl)-5-(4-methylpyridin-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 3.5 h / 20 °C 4.1: potassium acetate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / 1,4-dioxane / 2.75 h / 85 °C / Inert atmosphere; Sealed tube 5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,2-dimethoxyethane / 17 h / 85 °C / Sealed tube; Inert atmosphere

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

7
[ 944276-67-9 ]
2-(4'-((3,5-dimethyl-1H-1,2,4-triazol-1-yl)methyl)-6-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-3-yl)-4-methylpyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 °C / Inert atmosphere 3.2: 3.5 h / 20 °C 4.1: potassium acetate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / 1,4-dioxane / 2.75 h / 85 °C / Inert atmosphere; Sealed tube 5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / water; 1,2-dimethoxyethane / 17 h / 85 °C / Sealed tube; Inert atmosphere 6.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 17 h / 120 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

8
[ 944276-67-9 ]
2-ethyl-3-((5'-(6-methoxypyridin-2-yl)-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 3 h / 110 °C / Inert atmosphere; Sealed tube 4.2: 0.17 h
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 3 h / 110 °C / Inert atmosphere; Sealed tube 5.2: 0.17 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

9
[ 944276-67-9 ]
5-bromo-4'-((2,4-dimethyl-6-oxopyrimidin-1(6H)-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h 3.2: 0.5 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

10
[ 944276-67-9 ]
4'-((2,4-dimethyl-6-oxopyrimidin-1(6H)-yl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h 3.2: 0.5 h 4.1: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

11
[ 944276-67-9 ]
4"-((2,4-dimethyl-6-oxopyrimidin-1(6H)-yl)methyl)-[1,1':3',1"-terphenyl]-4'-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h 3.2: 0.5 h 4.1: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C 5.1: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

12
[ 944276-67-9 ]
3-((6'-(2H-tetrazol-5-yl)-[1,1':3',1"-terphenyl]-4-yl)methyl)-2,6-dimethylpyrimidin-4(3H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h 3.2: 0.5 h 4.1: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C 5.1: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C 6.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 100 °C / Sealed tube

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

13
[ 944276-67-9 ]
2-ethyl-5,7-dimethyl-3-((5'-(pyridin-2-yl)-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 3 h / 110 °C / Inert atmosphere; Sealed tube 4.2: 0.33 h
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 3 h / 110 °C / Inert atmosphere; Sealed tube 5.2: 0.33 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

14
[ 944276-67-9 ]
3-((5'-(3,3-difluoropyrrolidin-1-yl)-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation; sodium t-butanolate / tetrahydrofuran / 1.5 h / 65 °C / Sealed tube 4.2: 0.17 h / 20 °C
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: chloro(2-dicyclohexylphosphino-2’,6’-diisopropoxy-1,1’-biphenyl)[2-(2’-amino-1,1‘-biphenyl)]palladium(II) 2nd generation; sodium t-butanolate / tetrahydrofuran / 1.5 h / 65 °C / Sealed tube 5.2: 0.17 h / 20 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

15
[ 944276-67-9 ]
C₂₄H₂₁BrN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

16
[ 944276-67-9 ]
C₂₄H₂₂BrN₇ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

17
[ 944276-67-9 ]
C₄₉H₄₈BN₇O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3: triethylamine / dichloromethane / 1 h 4: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)CH₂Cl₂ / 1,4-dioxane / 1.17 h / 130 °C / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: potassium acetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / 1,4-dioxane / 1.17 h / 130 °C / Inert atmosphere; Microwave irradiation

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

18
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

19
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(4-methoxypyridin-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C 3: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; water; ethanol / 2 h / 100 °C
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C 4.1: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; water; ethanol / 2 h / 100 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

20
[ 944276-67-9 ]
2-ethyl-3-((5'-(4-methoxypyridin-2-yl)-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C 3: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; water; ethanol / 2 h / 100 °C 4: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 1 h / 105 °C 4.1: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; water; ethanol / 2 h / 100 °C 5.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

21
[ 944276-67-9 ]
3-((6'-(2H-tetrazol-5-yl)-2",3",4",5"-tetrahydro-[1,1':3',1"-terphenyl]-4-yl)methyl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water; ethanol / 0.5 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation 4.2: 0.08 h
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water; ethanol / 0.5 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation 5.2: 0.08 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

22
[ 944276-67-9 ]
2-ethyl-5,7-dimethyl-3-((6'-(2-trityl-2H-tetrazol-5-yl)-2",3",4",5"-tetrahydro-[1,1':3',1"-terphenyl]-4-yl)methyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3: triethylamine / dichloromethane / 1 h 4: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water; ethanol / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water; ethanol / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

23
[ 944276-67-9 ]
3-((5'-cyclohexyl-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water; ethanol / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube 5.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; ethanol / 24 h 5.2: 0.08 h
	Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / toluene; water; ethanol / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube 6.1: palladium on activated charcoal; hydrogen / tetrahydrofuran; ethanol / 24 h 6.2: 0.08 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

24
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(tetrahydrofuran-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: Ir(dF(CF₃)ppy)2(bpy)PF₆; [nickel(II)dichloride(dimethoxyethane)]; 4,4'-di-tert-butyl-2,2'-bipyridine; caesium carbonate / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Microwave irradiation
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: Ir(dF(CF₃)ppy)2(bpy)PF₆; [nickel(II)dichloride(dimethoxyethane)]; 4,4'-di-tert-butyl-2,2'-bipyridine; caesium carbonate / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Microwave irradiation

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

25
[ 944276-67-9 ]
(S)-4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(tetrahydrofuran-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]
(R)-4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(tetrahydrofuran-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: Ir(dF(CF₃)ppy)2(bpy)PF₆; [nickel(II)dichloride(dimethoxyethane)]; 4,4'-di-tert-butyl-2,2'-bipyridine; caesium carbonate / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Microwave irradiation 3: chiral SFC (Regis Whelk-01, 21x250 mm, 5 micron column; 20percent MeOH / 80percent CO₂ mobile phase; 45 mL/min, 150 bar, 40 °C) / Resolution of racemate
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: Ir(dF(CF₃)ppy)2(bpy)PF₆; [nickel(II)dichloride(dimethoxyethane)]; 4,4'-di-tert-butyl-2,2'-bipyridine; caesium carbonate / N,N-dimethyl-formamide / 0.33 h / Inert atmosphere; Microwave irradiation 4.1: chiral SFC (Regis Whelk-01, 21x250 mm, 5 micron column; 20percent MeOH / 80percent CO₂ mobile phase; 45 mL/min, 150 bar, 40 °C) / Resolution of racemate

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

26
[ 944276-67-9 ]
5-(3,4-dihydro-2H-pyran-6-yl)-4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

27
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(tetrahydro-2H-pyran-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / methanol / 1 h
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen / methanol / 1 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

28
[ 944276-67-9 ]
(R)-4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(tetrahydro-2H-pyran-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]
(S)-4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(tetrahydro-2H-pyran-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C / Inert atmosphere 3: palladium on activated charcoal; hydrogen / methanol / 1 h 4: chiral SFC (Chiralcel OJ-H, 21x250 mm, 5 micron column; 20percent MeOH / 80percent C0₂ mobile phase; 45 mL/min, 120 bar, 40 °C) / Resolution of racemate
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / toluene; ethanol / 3 h / 100 °C / Inert atmosphere 4.1: palladium on activated charcoal; hydrogen / methanol / 1 h 5.1: chiral SFC (Chiralcel OJ-H, 21x250 mm, 5 micron column; 20percent MeOH / 80percent C0₂ mobile phase; 45 mL/min, 120 bar, 40 °C) / Resolution of racemate

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

29
[ 944276-67-9 ]
5-cyclopentyl-4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: Ir(dF(CF₃)ppy)2(bpy)PF₆; [nickel(II)dichloride(dimethoxyethane)]; 4,4'-di-tert-butyl-2,2'-bipyridine; tris-(trimethylsilyl)silane; sodium carbonate / 1,2-dimethoxyethane / 18 h / Inert atmosphere; Sealed tube; Microwave irradiation
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: Ir(dF(CF₃)ppy)2(bpy)PF₆; [nickel(II)dichloride(dimethoxyethane)]; 4,4'-di-tert-butyl-2,2'-bipyridine; tris-(trimethylsilyl)silane; sodium carbonate / 1,2-dimethoxyethane / 18 h / Inert atmosphere; Sealed tube; Microwave irradiation

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

30
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-N-phenyl-6-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-3-amine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: sodium t-butanolate; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / tetrahydrofuran / 1 h / 65 °C / Inert atmosphere 4.2: 1 h
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: sodium t-butanolate; [(2-di-cyclohexylphosphino-3,6-dimethoxy-2’,4’,6’-triisopropyl-1,1‘-biphenyl)-2-(2‘-amino-1,1’-biphenyl)]palladium(II) methanesulfonate / tetrahydrofuran / 1 h / 65 °C / Inert atmosphere 5.2: 1 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

31
[ 944276-67-9 ]
2-ethyl-3-((5'-(indolin-1-yl)-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: sodium t-butanolate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / tetrahydrofuran / 1 h / 65 °C / Inert atmosphere 4.2: 1 h
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: sodium t-butanolate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / tetrahydrofuran / 1 h / 65 °C / Inert atmosphere 5.2: 1 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

32
[ 944276-67-9 ]
2-ethyl-5,7-dimethyl-3-((5'-(4-methylpiperidin-1-yl)-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: sodium t-butanolate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate / tetrahydrofuran / 1 h / 65 °C / Inert atmosphere 4.2: 1 h
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: sodium t-butanolate; [(2-di-tert-butylphosphino-2′,4′,6′-triisopropyl-1, 1′-biphenyl)-2-(2′-amino-1,1′-biphenyl)] palladium(II) methanesulfonate / tetrahydrofuran / 1 h / 65 °C / Inert atmosphere 5.2: 1 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

33
[ 944276-67-9 ]
5-bromo-4'-((2-methyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h 3.2: 0.5 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

34
[ 944276-67-9 ]
4'-((2-methyl-4-oxo-1,3-diazaspiro[4.4]non-1-en-3-yl)methyl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: phosphorus tribromide / dichloromethane / 0.25 h / 0 - 20 °C 3.1: sodium hydride / N,N-dimethyl-formamide / 0.25 h 3.2: 0.5 h 4.1: potassium acetate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; XPhos / 1,4-dioxane / 2 h / 100 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

35
[ 944276-67-9 ]
3-((5'-bromo-2'-(2-trityl-2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3: triethylamine / dichloromethane / 1 h
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

36
[ 944276-67-9 ]
C₃₁H₂₆F₃N₇O [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3.1: triethylamine / dichloromethane / 1 h 4.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.5 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation 4.2: 0.17 h
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: potassium phosphate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 0.5 h / 120 °C / Inert atmosphere; Sealed tube; Microwave irradiation 5.2: 0.17 h

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

37
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-((trimethylsilyl)ethynyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere
	Multi-step reaction with 3 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

38
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-ethynyl-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 3: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C
	Multi-step reaction with 4 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

39
[ 944276-67-9 ]
5-(1-ethyl-1H-1,2,3-triazol-4-yl)-4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 3.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 4.1: dimethyl sulfoxide / 4 h / 20 °C 4.2: 16 h / 20 °C
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 5.1: dimethyl sulfoxide / 4 h / 20 °C 5.2: 16 h / 20 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

40
[ 944276-67-9 ]
2-ethyl-3-((5'-(1-ethyl-1H-1,2,3-triazol-4-yl)-2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 3.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 4.1: dimethyl sulfoxide / 4 h / 20 °C 4.2: 16 h / 20 °C 5.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 16 h / 120 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 5.1: dimethyl sulfoxide / 4 h / 20 °C 5.2: 16 h / 20 °C 6.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 16 h / 120 °C / Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

41
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(1-((trimethylsilyl)methyl)-1H-1,2,3-triazol-4-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 3: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 4: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 16 h / 20 °C
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 5.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 16 h / 20 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

42
[ 944276-67-9 ]
4'-((2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridin-3-yl)methyl)-5-(1-methyl-1H-1,2,3-triazol-4-yl)-[1,1'-biphenyl]-2-carbonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 3: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 4: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 16 h / 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Cooling with ice
	Multi-step reaction with 6 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 5.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 16 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Cooling with ice

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

43
[ 944276-67-9 ]
2-ethyl-5,7-dimethyl-3-((5'-(1-methyl-1H-1,2,3-triazol-4-yl)-2'-(1H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 6 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 3: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 4: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 16 h / 20 °C 5: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Cooling with ice 6: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 16 h / 120 °C / Inert atmosphere; Sealed tube
	Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: bis-triphenylphosphine-palladium(II) chloride; triethylamine; copper(l) iodide / tetrahydrofuran / 2 h / 70 °C / Inert atmosphere 4.1: potassium carbonate / tetrahydrofuran; methanol / 3 h / 20 °C 5.1: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; <i>tert</i>-butyl alcohol / 16 h / 20 °C 6.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Cooling with ice 7.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 16 h / 120 °C / Inert atmosphere; Sealed tube

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

44
[ 944276-67-9 ]
3-((5'-(1H-pyrazol-1-yl)-2'-(2H-tetrazol-5-yl)-[1,1'-biphenyl]-4-yl)methyl)-2-ethyl-5,7-dimethyl-3H-imidazo[4,5-b]pyridine [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / toluene; water; ethanol / 18 h / 100 °C / Inert atmosphere; Sealed tube 2: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 3: triethylamine / dichloromethane / 1 h 4: potassium carbonate; <i>L</i>-proline; copper(l) iodide / dimethyl sulfoxide / 48 h / 100 - 150 °C
	Multi-step reaction with 5 steps 1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / tetrahydrofuran; methanol / 1 h / 120 °C / Microwave irradiation; Sealed tube 2.1: sodium hydride / N,N-dimethyl-formamide / 1 h / 20 °C / Cooling with ice 2.2: 3 h / 0 - 20 °C 3.1: trimethylsilylazide; di(n-butyl)tin oxide / toluene / 18 h / 100 °C / Sealed tube; High pressure 4.1: triethylamine / dichloromethane / 1 h 5.1: potassium carbonate; <i>L</i>-proline; copper(l) iodide / dimethyl sulfoxide / 48 h / 100 - 150 °C

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1
[2]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1

45
[ 944276-67-9 ]
2-ethyl-5,7-dimethyl-3-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl)-3H-imidazo[4,5-b]pyridine [ No CAS ]
C₂₄H₂₁BrN₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
57%	With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ In ethanol; water; toluene at 100℃; for 18h; Inert atmosphere; Sealed tube;	055 Intermediate 055a: 4'-((2-Butyl-4-oxo-l,3-diazaspiro[4.4]non-l-en-3-yl)methyl)-5- carbonitrile Intermediate 001d (1 g, 2.56 mmol), 4-bromo-2-iodobenzonitrile (0.944 g, 3.07 mmol), and PdCl2(dppf)-CH2Cl2 Adduct (0.209 g, 0.256 mmol) were dissolved in toluene (20.4 mL), ethanol (5.11 mL), and tripotassium phosphate (2 M aq, 2.56 mL, 5.11 mmol) and the reaction was degassed for 15 minutes by bubbling with N2. The reaction was sealed and heated at 100 °C for 18 hours. The reaction was cooled to ambient temperature, filtered through celite, diluted with EtOAc, washed with saturated NaHCO3, then brine, dried (Na2SO4), filtered, and concentrated in vacuo. The crude material was purified by column chromatography (ISCO, 80 g silica gel column, 29 minute gradient of 0 to 100% EtOAc in hexanes) to yield Intermediate 055a (0.649 g, 1.49 mmol, 57%) as a tan solid. LC-MS (Method A2) RT = 0.85 min, MS (ESI) m/z: 445 (M+H)+. 1H NMR (500MHz, CDCl3) δ 7.66 (d, J=1.4 Hz, 1H), 7.64 - 7.58 (m, 2H), 7.51 - 7.47 (m, 2H), 7.27 (d, J=8.3 Hz, 2H), 6.94 (s, 1H), 5.55 (s, 2H), 2.84 (q, J=7.4 Hz, 2H), 2.67 (s, 3H), 2.62 (s, 3H), 1.36 (t, J=7.6 Hz, 3H)

Reference： [1]Current Patent Assignee: BRISTOL-MYERS SQUIBB CO; UNIVERSITY OF MONTREAL - WO2018/5591, 2018, A1 Location in patent: Page/Page column 147-149

46
[ 304858-65-9 ]
[ 944276-67-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With hydrogenchloride; potassium iodide; sodium nitrite; In water; at 0 - 20℃;	To a mixture of <strong>[304858-65-9]2-amino-4-bromobenzonitrile</strong> (1.00 g, 5.08 mmol) in 4 M aqueous HQ (7.5 mL) cooled at 0C was added a solution of sodium nitrite (0.490 g, 7.11 mmol) in H2O (3 mL), followed after 10 min by the dropwise addition of a solution of potassium iodide (2.106 g, 12.69 mmol) in H20 (3 mL). The reaction mixture was subsequently allowed to warm to RT and then it was extracted with EtOAc (50 mL). The organic layer was separated, washed (10% aqueous Na2S205, brine), dried (Na2S04) and evaporated under reduced pressure. The residue obtained was purified by flash chromatography (ISCO, 0 to 100 % EtOAc-hexane) to provide 4-bromo-2-iodobenzonitrile (1.17 g, 3.81 mmol, 75% yield). LC-MS (Method H): 1.239 min, [M + H]+= no ion observed. H NMR (400 MHz, CDC13) delta ppm 7.46 (d, 7= 8.22 Hz, 1H), 7.61 (dd, 7= 8.22 Hz, 1.76 Hz, 1H), 8.10 (d, 7= 1.96 Hz, 1H).

Reference： [1]Patent: WO2018/5591,2018,A1 .Location in patent: Page/Page column 348-349

47
[ 866625-02-7 ]
[ 944276-67-9 ]
5'-bromo-4-chloro-2'-cyanobiphenyl-2-carboxylic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
36%	With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In 1,4-dioxane; water; at 80℃; for 1.0h;Inert atmosphere;	General procedure: Under inert atmosphere, a mixture of halogeno-benzonitrile A (1.0 equiv.), boronic acid derivative B1 (1.1 equiv.) and PdCI2(dppf).CH2CI2 (0.10 equiv.) in a mixture of dioxane (0.10 mol.L"1) and aqueous K2C03 (1.2 mol.L"1) was heated at 80 C for 1 hour. After cooling to room temperature, the reaction mixture was hydrolyzed and extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over MgS04, concentrated and purified to afford the product.

Reference： [1]Patent: WO2018/206820,2018,A1 .Location in patent: Page/Page column 213; 214

48
[ 623-00-7 ]
[ 944276-67-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-iodo-succinimide; palladium diacetate; toluene-4-sulfonic acid In 1,2-dichloro-ethane at 70℃; for 72h;	98; 99 Example 98: Preparation of 4-cyano-2-((1,1-dimethylethyl)sulfonamido)-N-(3-phenylbicyclo[1.1.1]pentan-1-yl)benzamide 4-Bromobenzonitrile (1.068 g, 5.867 mmol), N-iodosuccinimide (1.452 g, 6.464 mmol), palladium(II) acetate (0.066 g, 0.29 mmol), and p-toluenesulfonic acid monohydrate (0.558 g, 2.94 mmol) were treated with 23 mL of 1,2-dichloroethane. The mixture was stirred at 70° C. for 72 hours. The reaction was then concentrated to a residue, which was purified by silica flash chromatography to afford 4-bromo-2-iodobenzonitrile. This compound was reacted following Step 1 through Step 3 of General Synthesis 3 to afford 4-bromo-2-((1,1-dimethylethyl)sulfonamido)benzoic acid. A solution of 4-bromo-2-((1,1-dimethylethyl)sulfonamido)benzoic acid (0.123 g, 0.366 mmol) in DMF was treated with copper(I) cyanide (0.098 g, 1.1 mmol). The mixture was stirred at 150° C. for 18 hours. The reaction was then acidified with 1 M aqueous hydrochloric acid. The aqueous phase was extracted 3× with ethyl acetate. The organic phases were combined and concentrated to a residue. The crude product was purified by silica flash chromatography to afford 4-cyano-2-((1,1-dimethylethyl)sulfonamido)benzoic acid, which was reacted according to Step 4 of General Synthesis 3 to afford 4-cyano-2-((1,1-dimethylethyl)sulfonamido)-N-(3-phenylbicyclo[1.1.1]pentan-1-yl)benzamide as a solid. 1H NMR (400 MHz, DMSO-d6) δ 11.01 (s, 1H), 9.77 (s, 1H), 8.00 (s, 1H), 7.96 (d, J=8.2 Hz, 1H), 7.67 (d, J=8.0 Hz, 1H), 7.36-7.19 (m, 5H), 2.38 (s, 6H), 1.30 (s, 9H). LCMS-ESI- (m/z): [M-H]- calcd 422.15; found 422.29.

Reference： [1]Current Patent Assignee: THE LIVER INC - US2019/359565, 2019, A1 Location in patent: Paragraph 0462; 0463

49
[ 944276-67-9 ]
[ 7211-39-4 ]
4-bromo-2-(dimethylphosphoryl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
51%	With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane at 100℃; for 12h;

Reference： [1]Stambirskyi, Maksym V.; Kostiuk, Tetiana; Sirobaba, Serhii I.; Rudnichenko, Alexander; Titikaiev, Dmytro L.; Dmytriv, Yurii V.; Kuznietsova, Halyna; Pishel, Iryna; Borysko, Petro; Mykhailiuk, Pavel K. [Journal of Organic Chemistry, 2021, vol. 86, # 18, p. 12783 - 12801]

50
[ 944276-67-9 ]
[ 122-01-0 ]
4-bromo-2-(4-chlorobenzoyl)benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
76%	Stage #1: 4-bromo-2-iodobenzonitrile With di-sec-butylmagnesium In toluene at -78℃; for 0.166667h; Schlenk technique; Stage #2: 4-chloro-benzoyl chloride With copper (I) cyanide di(lithium chloride)complex In tetrahydrofuran; toluene at 20℃;	Typical Procedure 1: Preparation of Diorganomagnesium Species by Halide/Magnesium Exchange Followed by Electrophilic Functionalization General procedure: A dry and argon-flushed Schlenk-flask equipped with a magnetic stirring bar and a septum was charged with the corresponding (hetero)aryl or alkenyl halide (1.00 equiv) and dissolved in dry toluene at the indicated concentration. When necessary, DMPU was added (detailed for each compound thereafter). Then, the exchange reagent R2Mg (R=sBu, 1c; R=Mes, 1d 0.60-0.70 equiv) was added dropwise at the indicated temperature and the reaction stirred for the indicated time. Subsequent reactions with electrophiles were carried out under the indicated conditions. The mixture was then quenched with a sat. aq. NH 4 Cl solution (10 mL), diluted with water (10 mL) and extracted with ethyl acetate (3 x 30 mL). The combined organic extracts were dried over Na 2 SO 4 , filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel using the appropriate eluent.

Reference： [1]Desaintjean, Alexandre; Danton, Fanny; Knochel, Paul [Synthesis, 2021, vol. 53, # 23, p. 4461 - 4476]

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
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CAS No. :	944276-67-9	MDL No. :	MFCD09907887
Formula :	C₇H₃BrIN	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	AAUCVXUNVYKWPB-UHFFFAOYSA-N
M.W :	307.91	Pubchem ID :	91882193
Synonyms :

Num. heavy atoms :	10
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 :	51.57
TPSA :	23.79 Å²

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	Yes
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.06 cm/s

Log Po/w (iLOGP) :	2.16
Log Po/w (XLOGP3) :	2.98
Log Po/w (WLOGP) :	2.93
Log Po/w (MLOGP) :	3.08
Log Po/w (SILICOS-IT) :	3.44
Consensus Log Po/w :	2.92

[ CAS No. 944276-67-9 ] {[proInfo.proName]}

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[ 944276-67-9 ] Synthesis Path-Downstream 1~50

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[ 944276-67-9 ]

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

Log S (ESOL) :	-4.07
Solubility :	0.0262 mg/ml ; 0.000085 mol/l
Class :	Moderately soluble
Log S (Ali) :	-3.14
Solubility :	0.221 mg/ml ; 0.000719 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-4.27
Solubility :	0.0165 mg/ml ; 0.0000536 mol/l
Class :	Moderately soluble

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	0.0
Synthetic accessibility :	2.17

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P280-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302	Packing Group:	N/A
GHS Pictogram:

Precautionary Statements-General
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P342	If experiencing respiratory symptoms:
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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.
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P370	In case of fire:
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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
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P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
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P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

[ CAS No. 944276-67-9 ] {[proInfo.proName]}

Quality Control of [ 944276-67-9 ]

Related Doc. of [ 944276-67-9 ]

Product Details of [ 944276-67-9 ]

Calculated chemistry of [ 944276-67-9 ]

Physicochemical Properties

Pharmacokinetics

Lipophilicity

Druglikeness

Water Solubility

Medicinal Chemistry

Safety of [ 944276-67-9 ]

Application In Synthesis of [ 944276-67-9 ]

[ 944276-67-9 ] Synthesis Path-Downstream 1~50

Related Functional Groups of [ 944276-67-9 ]

Aryls

Bromides

Iodides

Nitriles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 944276-67-9 ]