[ CAS No. 53484-16-5 ] {[proInfo.proName]}

Name: 53484-16-5|6-Bromo-1-methyl-1H-benzo[d]imidazole|95%
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SKU: A311530
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Product Details of [ 53484-16-5 ]

CAS No. :	53484-16-5	MDL No. :	MFCD09027271
Formula :	C₈H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	QDXJAGXUNYFXRG-UHFFFAOYSA-N
M.W :	211.06	Pubchem ID :	23537644
Synonyms :

Safety of [ 53484-16-5 ]

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

Application In Synthesis of [ 53484-16-5 ]

* 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 [ 53484-16-5 ]
Downstream synthetic route of [ 53484-16-5 ]

[ 53484-16-5 ] Synthesis Path-Upstream 1~8

1
[ 4887-88-1 ]
[ 74-88-4 ]
[ 53484-15-4 ]
[ 53484-16-5 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6334 - 6353

2
[ 337915-79-4 ]
[ 149-73-5 ]
[ 53484-16-5 ]

Yield	Reaction Conditions	Operation in experiment
54.74%	With toluene-4-sulfonic acid In toluene for 2 h; Heating / reflux	To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCI₂.2H₂O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and 1N NaOH (100ml). After extraction with CH₂CI₂, the organic phase was dried over Na₂SO₄ and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH₂CI₂/MeOH (95/5). The title compound was obtained as a cream powder (2.5g, 54.74percent); m.p. 126-128°C.
54.74%	With toluene-4-sulfonic acid In toluene for 2 h; Heating / reflux	To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCl₂.2H₂O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and NaOH 1N (100ml). After extraction with CH₂CI₂, the organic phase was dried over Na₂SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH₂CI₂/MeOH (95/5). The title compoundwas obtained as a cream powder (2.5g, 54.74percent); m.p. 126-128°C

Reference： [1] Patent: WO2004/111036, 2004, A1, . Location in patent: Page 21
[2] Patent: WO2004/111046, 2004, A2, . Location in patent: Page/Page column 18-19
[3] Patent: WO2014/100734, 2014, A1, . Location in patent: Paragraph 00320
[4] Patent: WO2015/200677, 2015, A2, . Location in patent: Paragraph 00459; 00460

3
[ 302800-13-1 ]
[ 149-73-5 ]
[ 53484-16-5 ]

Yield	Reaction Conditions	Operation in experiment
44%	Stage #1: With tin(ll) chloride In ethanol at 80℃; for 4 h; Stage #2: With toluene-4-sulfonic acid In toluene at 110℃; for 15 h;	Step 3: 6-Bromo-l-methyl-117-benzoimidazole; [0311] To a suspension of (5-bromo-2-nitro-phenyl)-methyl-amine (1.2 g, 5.19 mmol) in ethanol (25 mL) was added tin(II) chloride (1.97 g, 10.39 mmol). The reaction mixture was stirred at 8O⁰C for 4h, then it was concentrated in vacuo. To the residue was added toluene (12 mL), trimethyl orthoformate (0.625 mL, 5.71 mmol), and para-toluenesulfonic acid (49 mg, 0.26 mmol). The reaction mixture was stirred at HO⁰C for 15h, then it was concentrated in vacuo and the residue was adsorbed on silica gel. Purification by flash chromatography on silica gel using a gradient of 0-8percent methanol/dichloromethane afforded 482 mg of 6- bromo-1 -methyl- l//-benzoimidazole as a dark orange solid (44percent yield): ¹H NMR (DMSO- EPO <DP n="84"/>d6) δ 3.83 (s, 3H), 7.33 (dd, IH), 7.59 (d, IH), 7.86 (d, IH), 8.21 (s, IH); MS (m/z) 211, 213 [M+H⁺]⁺.

Reference： [1] Patent: WO2008/51808, 2008, A2, . Location in patent: Page/Page column 82-83

4
[ 64-18-6 ]
[ 302800-13-1 ]
[ 53484-16-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron; ammonium chloride In isopropyl alcohol for 24 h; Reflux	[0444j Step B: Preparation of 6-bromo-1-methyl-benzimidazole: A mixture of 5- bromo-N-methyl-2-nitro-aniline (6.0 g, 26 mmol), iron powder (14.5 g, 260 mmol), ammonium chloride (13.9 g, 260 mmol) and formic acid (49.0 mL, 1298 mmol) in 2- propanol (75 mL) was stirred under reflux for 24 hours. After cooling to ambient temperature, ethyl acetate (50 mL) was added. The solid was removed by filtering through a pad of celite. The filtrate was concentrated. Saturated sodium bicarbonate (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by flash chromatography on silica gel 10:1 ethyl acetate/MeOH to give 6-bromo-1-methyl-benzimidazole (5.35 g, 98percent) as solid.

Reference： [1] Patent: WO2015/175845, 2015, A1, . Location in patent: Paragraph 0444

5
[ 321-23-3 ]
[ 53484-16-5 ]

Reference： [1] Patent: WO2014/100734, 2014, A1,
[2] Patent: WO2015/175845, 2015, A1,
[3] Patent: WO2015/200677, 2015, A2,

6
[ 4887-88-1 ]
[ 74-88-4 ]
[ 53484-15-4 ]
[ 53484-16-5 ]

Reference： [1] Journal of Organic Chemistry, 2018, vol. 83, # 12, p. 6334 - 6353

7
[ 302800-13-1 ]
[ 53484-16-5 ]

Reference： [1] Patent: WO2014/100734, 2014, A1,
[2] Patent: WO2015/200677, 2015, A2,

8
[ 53484-16-5 ]
[ 26530-93-8 ]

Reference： [1] Patent: WO2016/57834, 2016, A1, . Location in patent: Paragraph 000390

[ 53484-16-5 ] Synthesis Path-Downstream 1~47

2
[ 7486-35-3 ]
[ 53484-16-5 ]
[ 813449-02-4 ]

Yield	Reaction Conditions	Operation in experiment
96.1%	tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; for 24h;Heating / reflux;	To a solution of intermediate 5 (2.5g, 11.8 mmol) in dioxane (100ml) were added tributyl(vinyl)tin (5.2ml, 18 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.69g, 0.5mmol) and the mixture was heated under reflux for 24 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2CI2/MeOH (95/5). The title compound was obtained as an oil (1.8g, 96.1percent); NMR H1 (300MHz, CDCI3, ppm) 8: 7.9 (s, 1H), 7.75 (d, 1H), 7.4 (m, 2H), 6.85 (dd, 1 H), 5.8 (d, 1 H), 5.25 (d, 1 H), 3.85 (s, 3H). .
96.1%	tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; for 24h;Heating / reflux;	To a solution of intermediate 5 (2.5g, 11.8 mmol) in dioxane (100ml) were addedtributyl(vinyl)tin (5,2ml, 18 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.69g, O.Smmol) and the mixture was heated under reflux for 24 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel, eluting with CH2CI2/MeOH (95/5). The title compound was obtained as an oil (1.8g, 96.1percent); NMR H1 (300MHz, CDCI3, ppm) 5: 7.9 (s, 1H), 7.75 (d, 1H), 7.4 (m, 2H), 6.85 (dd, 1H), 5.8 (d, 1H), 5.25 (d, 1H), 3.85 (s, 3H).

Reference： [1]Patent: WO2004/111036,2004,A1 .Location in patent: Page 22
[2]Patent: WO2004/111046,2004,A2 .Location in patent: Page/Page column 19-20

3
[ 337915-79-4 ]
[ 149-73-5 ]
[ 53484-16-5 ]

Yield	Reaction Conditions	Operation in experiment
54.74%	With toluene-4-sulfonic acid; In toluene; for 2h;Heating / reflux;	To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCI2.2H2O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and 1N NaOH (100ml). After extraction with CH2CI2, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2/MeOH (95/5). The title compound was obtained as a cream powder (2.5g, 54.74percent); m.p. 126-128°C.
54.74%	With toluene-4-sulfonic acid; In toluene; for 2h;Heating / reflux;	To a solution of intermediate 2 (5g, 21.6mmol) in EtOH (200ml) was added portionwise SnCl2.2H2O (9.8g, 43mmol) and the mixture was heated under reflux for 4 hours and then concentrated under reduced pressure. The residue was treated with water (200ml) and NaOH 1N (100ml). After extraction with CH2CI2, the organic phase was dried over Na2SO4 and concentrated under reduced pressure. The residue was dissolved in toluene (50ml) and trimethylorthoformate (2.6ml, 24 mmol) and ARTS (0.2g) were added and the mixture was heated under reflux for 2 hours and then concentrated under reduced pressure. The residue was purified by chromatography on silica gel eluting with CH2CI2/MeOH (95/5). The title compoundwas obtained as a cream powder (2.5g, 54.74percent); m.p. 126-128°C
	With toluene-4-sulfonic acid; at 100℃; for 4h;	[00320] To a solution of 5-bromo-Nl-methylbenzene-l,2-diamine (7.4 g, 37 mmol) in trimethyl orthoformate (100 mL) was added p-toluenesulfonic acid (0.36g, 1.9 mmol). The reaction mixture was heated at 100 °C for 4 h, cooled, concentrated, dissolved in ethyl acetate, washed with brine, dried over sodium sulfate and concentrated. The crude product was used in next step without further purification. (7.3 g, yield 93percent) MS (ESI+) e/z: 212.1.

With toluene-4-sulfonic acid; at 100℃; for 4h;

To a solution of <strong>[337915-79-4]5-bromo-N1-methylbenzene-1,2-diamine</strong> (7.4 g, 37 mmol) in HC(OMe)3 (100 mL) was added TsOH (0.36 g, 1.9 mmol). The reaction mixture was heated at 100 °C for 4 h and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate (200 mL), washed with brine, dried over Na2SO4, and concentrated. The crude product was used in next step without further purification (7.3 g, 93percent). LCMS (mlz): 212.1 (M+ 1).

Reference： [1]Patent: WO2004/111036,2004,A1 .Location in patent: Page 21
[2]Patent: WO2004/111046,2004,A2 .Location in patent: Page/Page column 18-19
[3]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00320
[4]Patent: WO2015/200677,2015,A2 .Location in patent: Paragraph 00459; 00460

4
[ 302800-13-1 ]
[ 149-73-5 ]
[ 53484-16-5 ]

Yield	Reaction Conditions	Operation in experiment
44%		Step 3: 6-Bromo-l-methyl-117-benzoimidazole; [0311] To a suspension of (5-bromo-2-nitro-phenyl)-methyl-amine (1.2 g, 5.19 mmol) in ethanol (25 mL) was added tin(II) chloride (1.97 g, 10.39 mmol). The reaction mixture was stirred at 8O0C for 4h, then it was concentrated in vacuo. To the residue was added toluene (12 mL), trimethyl orthoformate (0.625 mL, 5.71 mmol), and para-toluenesulfonic acid (49 mg, 0.26 mmol). The reaction mixture was stirred at HO0C for 15h, then it was concentrated in vacuo and the residue was adsorbed on silica gel. Purification by flash chromatography on silica gel using a gradient of 0-8percent methanol/dichloromethane afforded 482 mg of 6- bromo-1 -methyl- l//-benzoimidazole as a dark orange solid (44percent yield): 1H NMR (DMSO- EPO <DP n="84"/>d6) delta 3.83 (s, 3H), 7.33 (dd, IH), 7.59 (d, IH), 7.86 (d, IH), 8.21 (s, IH); MS (m/z) 211, 213 [M+H+]+.

Reference： [1]Patent: WO2008/51808,2008,A2 .Location in patent: Page/Page column 82-83

5
[ 53484-16-5 ]
[ 10406-94-7 ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; copper(l) chloride; In 1-methyl-pyrrolidin-2-one; at 200℃; for 1.5h;Microwave irradiation; Inert atmosphere;	A microwave flask was charged with copper(l) chloride (1.87 g, 18.95 mmol), copper(l) iodide (0.36 g, 1.895 mmol) and 6-bromo-1-rnethyl-benzirnidazole (2.00 g, 9.48 mmol), and the vial was flushed with nitrogen. NMP (18 mL) was added. The flask was heated under microwave irradiation to 200 0C for 1.5 h. The mixture was diluted with ethyl acetate (1.5 L) and a 9:1 saturated aqueous ammonium chloride- ammonium hydroxide solution was added (0.25 L). The mixture was stirred vigorously for 15 min and filtered through celite. The two phases were separated and the organic phase was washed with water (0.2 L5). The combined organic phase was dried over MgSO4, filtered and concentrated to give a moist pale brown solid, contaminated with NMP. The solid was redissolved in ethyl acetate and washed with water. The organic phase was dried over MgSO4, filtered and concentrated to give 6-chloro-1-methyl-1H-benzo[d]imidazole. ESI- MS: m/z 167.1, (M+H).

Reference： [1]Patent: WO2010/130796,2010,A1 .Location in patent: Page/Page column 99-100

6
[ 53484-16-5 ]
[ 912333-44-9 ]

Reference： [1]Patent: WO2010/130796,2010,A1

7
[ 53484-16-5 ]
[ 1255871-21-6 ]

Reference： [1]Patent: WO2010/130796,2010,A1

8
[ 53484-16-5 ]
[ 1255870-11-1 ]

Reference： [1]Patent: WO2010/130796,2010,A1

9
[ 53484-16-5 ]
[ 1616099-44-5 ]

Reference： [1]Patent: WO2014/100695,2014,A1

10
[ 53484-16-5 ]
[ 1616098-45-3 ]

Reference： [1]Patent: WO2014/100695,2014,A1

11
[ 53484-16-5 ]
[ 1616096-77-5 ]

Reference： [1]Patent: WO2014/100695,2014,A1

12
[ 30418-59-8 ]
[ 53484-16-5 ]
[ 1616099-43-4 ]

Yield	Reaction Conditions	Operation in experiment
56.7%	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In 1,4-dioxane; at 120℃; for 0.5h;Microwave irradiation;	To a solution of 6-bromo-l -methyl- lH-benzo[d] imidazole (500 mg, 2.37 mmol) in dioxane(10 mL) was added (3-aminophenyl)boronic acid (320 mg, 2.34 mmol), 2N K2CO3 (2 mL, 4mmol) and PdCl2(dppf) (50 mg, 0.063 mmol). The reaction mixture was heated at 120°C under microwave conditions for 30 min. The cooled mixture was concentrated under reduced pressure and the residue dissolved in ethyl acetate, washed with water with the separated organic layers being dried and concentrated to afford the desired product as a brown solid (300 mg, 56.7percent). LCMS (m/z): 224.1 [M+H]+

Reference： [1]Patent: WO2014/100695,2014,A1 .Location in patent: Paragraph 00457

13
[ 302800-13-1 ]
[ 53484-16-5 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]Patent: WO2015/200677,2015,A2

14
[ 321-23-3 ]
[ 53484-16-5 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]Patent: WO2015/175845,2015,A1
[3]Patent: WO2015/200677,2015,A2

15
[ 53484-16-5 ]
[ 1616059-85-8 ]

Reference： [1]Patent: WO2014/100734,2014,A1

16
[ 53484-16-5 ]
[ 1616059-33-6 ]

Reference： [1]Patent: WO2014/100734,2014,A1

17
[ 53484-16-5 ]
[ 1616059-76-7 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]Patent: WO2015/200677,2015,A2

18
[ 53484-16-5 ]
[ 1616059-77-8 ]

Reference： [1]Patent: WO2014/100734,2014,A1
[2]Patent: WO2015/200677,2015,A2

19
[ 53484-16-5 ]
[ 1616059-43-8 ]

Reference： [1]Patent: WO2014/100734,2014,A1

20
[ 73183-34-3 ]
[ 53484-16-5 ]
[ 1107627-01-9 ]

Yield	Reaction Conditions	Operation in experiment
6 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100℃; for 3h;	[00321] To a solution of 6-bromo-l -methyl- lH-benzo[d] imidazole (5 g, 23.8 mmol) in dioxane (60 mL) was added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(l,3,2-dioxaborolane) (9.1 g, 35.7 mmol), Pd(dppf)Cl2 (0.5 g) and potassium acetate (4.67 g, 47.6 mmol). The reaction mixture was heated at 100 °C for 3 h, cooled and concentrated. The crude reaction mixture was purified by column chromatography. (6 g, yield 98percent) MS (ESI+) e/z: 259.1.
6 g	With [1,1'-bis(diphenylphosphino)ferrocene]dichloropalladium(II); potassium acetate; In 1,4-dioxane; at 100℃; for 3h;Inert atmosphere;	To a solution of <strong>[53484-16-5]6-bromo-1-methyl-1H-benzo[d]imidazole</strong> (5 g, 23.8 mmol) in dioxane (60 mL) was added 4,4,4?,4?,5,5,5?,5?-octamethyl-2,2?-bi(1,3,2-dioxaborolane) (9.1 g, 35.7 mmol), Pd(dppf)C12 (0.5 g) and KOAc (4.67 g, 47.6 mmol). The reaction mixture was heated at 100 °C under nitrogen for 3 h until the reaction appeared complete by TLC analysis. The solvent was evaporated and the resulting residue was purified by flash chromatography on Si02 to afford the desired product (6 g, 93percent) as a pale solid. LCMS (m/z): 259.1 (M+1).

Reference： [1]Patent: WO2014/100734,2014,A1 .Location in patent: Paragraph 00321
[2]Patent: WO2015/200677,2015,A2 .Location in patent: Paragraph 00461; 00462

21
[ 3544-25-0 ]
[ 53484-16-5 ]
2-[4-[(3-methylbenzimidazol-5-yl)amino]phenyl]acetonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	3.1. Compound A 2-[4-[(3-methylbenzimidazol-5-yl)amino]phenyl]acetonitrile A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1,4-dioxane (1 mL) was sonicated and added under nitrogen to a mixture of <strong>[53484-16-5]6-bromo-1-methyl-benzimidazole</strong> (0.45 mmol), 2-(4-aminophenyl)acetonitrile (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 110° C. for 12 h. The mixture was diluted (DCM), washed (H2O), dried (phase separator and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound A). MW: 262.3. MS Ms'd: 263.2. NMR: 1H NMR (400 MHz, DMSO-d6): delta=8.13 (1H, s), 7.68 (1H, dd), 7.60 (1H, dd), 7.54 (1H, d), 7.32 (1H, d), 7.24 (1H, t), 6.91 (1H, dd), 3.77 (3H, s), 3.39 (3H, s).
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; Sonication;	3.1. Compound A 2-[4-[(3-methylbenzimidazol-5-yl)amino]phenyl]acetonitrile j00313j A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1,4-dioxane (1 mL) was sonicated and added under nitrogen to a mixture of 6-bromo- 1 -methyl-benzimidazole (0.45 mmol), 2-(4-aminophenyl)acetonitrile (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 110°C for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound A).j00314j MW: 262.3. MS Ms?d: 263.2.j00315j NMR: 1HNMR (400 MHz, DMSO-d6): = 8.13 (1 H, s), 7.68(1 H, dd), 7.60(1 H, dd), 7.54 (1 H, d), 7.32 (1 H, d), 7.24 (1 H, t), 6.91 (1 H, dd), 3.77 (3 H, s), 3.39 (3 H, s).
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1 ,4-dioxane (1 mE) was sonicated and added undernitrogen to a mixture of <strong>[53484-16-5]6-bromo-1-methyl-benzimidazole</strong> (0.45 mmol), 2-(4-aminophenyl)acetonitrile (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mE). The mix-ture was stirred at 1100 C. for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator and concentrated. The residue was purified by prep HPEC to yield the desired product (Compound A).MW: 262.3. MS Ms?d: 263.2.NMR: 1H NMR (400 MHz, DMSO-d6): oe=8.13 (1H, s), 7.68 (1H, dd), 7.60 (1H, dd), 7.54 (1H, d), 7.32 (1H, d), 7.24 (1H, t), 6.91 (1H, dd), 3.77 (3H, s), 3.39 (3H, s).

Reference： [1]Patent: US2015/203455,2015,A1 .Location in patent: Paragraph 0536-0539
[2]Patent: WO2015/110378,2015,A1 .Location in patent: Paragraph 00313; 00314; 00315
[3]Patent: US9440929,2016,B2 .Location in patent: Page/Page column 123

22
[ 63069-50-1 ]
[ 53484-16-5 ]
3-fluoro-4-[methyl-(3-methylbenzimidazol-5-yl)amino]benzonitrile [ No CAS ]

Reference： [1]Patent: US2015/203455,2015,A1
[2]Patent: WO2015/110378,2015,A1
[3]Patent: US9440929,2016,B2

23
[ 63069-50-1 ]
[ 53484-16-5 ]
3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With palladium diacetate; caesium carbonate; XPhos; In toluene; at 110℃; for 16h;	Step i: 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile A mixture containing <strong>[53484-16-5]6-bromo-1-methyl-benzimidazole</strong> (2.38 mmol), 4-amino-3-fluoro-benzonitrile (3.57 mmol), XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mL) was stirred at 110° C. for approximately 16 h. The mixture was diluted (EtOAc), washed (H2O), dried (Na2SO4) and concentrated to yield the desired product 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile.
	With palladium diacetate; caesium carbonate; XPhos; In toluene; at 110℃; for 16h;	3.3.1. Step i. 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrilej00319j A mixture containing <strong>[53484-16-5]6-bromo-1-methyl-benzimidazole</strong> (2.38 mmol), 4-amino-3-fluoro- benzonitrile (3.57 mmol), XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mL) was stirred at 110°C for approximately 16 h. The mixture was diluted (EtOAc), washed (H20), dried (Na2SO4) and concentrated to yield the desired product 3-fluoro-4-[(3-methylbenzimidazol- 5-yl)amino]benzonitrile.
	With palladium diacetate; caesium carbonate; XPhos; In toluene; at 110℃; for 0.16h;	A mixture containing 6-bromo-1 -methyl-benzimidazole (2.38 mmol), 4-amino-3-fluoro-benzonitrile (3.57 mmol),XPhos (0.95 mmol), Cs2CO3 (7.14 mmol) and Pd(OAc)2 (0.71 mmol) in dry toluene (8 mE) was stirred at 1100 C. forapproximately 16 h. The mixture was diluted (EtOAc), washed (H20), dried (Na2SO4) and concentrated to yield thedesired product 3-fluoro-4-[(3-methylbenzimidazol-5-yl)amino]benzonitrile.

Reference： [1]Patent: US2015/203455,2015,A1 .Location in patent: Paragraph 0544-0545
[2]Patent: WO2015/110378,2015,A1 .Location in patent: Paragraph 00319
[3]Patent: US9440929,2016,B2 .Location in patent: Page/Page column 124

24
[ 22013-33-8 ]
[ 53484-16-5 ]
C₁₆H₁₅N₃O₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere;	A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1,4-dioxane (1 mL) was sonicated and added under nitrogen to a mixture of <strong>[53484-16-5]6-bromo-1-methyl-benzimidazole</strong> (0.45 mmol), 2,3-dihydro-1,4-benzodioxin-6-amine (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 110° C. for 12 h. The mixture was diluted (DCM), washed (H2O), dried (phase separator and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound B). [0542] MW: 281.3. MS Ms?d: 282.1. [0543] NMR: 1H NMR (400 MHz, DMSO-d6): delta=7.94 (1H, s), 7.80 (1H, br s), 7.45 (1H, d), 7.05 (1H, d), 6.86 (1H, dd), 6.73 (1H, dd), 6.61-6.57 (2H, m), 4.22-4.16 (4H, m), 3.71 (3H, s).
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; Sonication;	3.2. Compound B j00316j A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1,4-dioxane (1 mL) was sonicated and added under nitrogen to a mixture of 6-bromo- 1 -methyl-benzimidazole (0.45 mmol), 2,3-dihydro-1,4-benzodioxin-6-amine (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mL). The mixture was stirred at 110°C for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator and concentrated. The residue was purified by prep HPLC to yield the desired product (Compound B).j00317j MW: 281.3. MS Ms?d: 282.1.j00318j NMR: 1H NMR (400 MHz, DMSO-d6): = 7.94 (1 H, s), 7.80 (1 H, br s), 7.45 (1 H, d), 7.05 (1 H, d), 6.86 (1 H, dd), 6.73 (1 H, dd), 6.61-6.57 (2 H, m), 4.22-4.16 (4 H, m), 3.71 (3 H, s).
	With tris-(dibenzylideneacetone)dipalladium(0); caesium carbonate; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 110℃; for 12h;Inert atmosphere; Microwave irradiation;	A mixture of Pd2(dba)3 (0.01 mmol) and Xantphos (0.01 mmol) in 1 ,4-dioxane (1 mE) was sonicated and added undernitrogen to a mixture of <strong>[53484-16-5]6-bromo-1-methyl-benzimidazole</strong> (0.45 mmol), 2,3-dihydro-1 ,4-benzodioxin-6-amine (0.58 mmol) and Cs2CO3 (0.62 mmol) in 1,4-dioxane (2 mE). The mixture was stirred at 1100 C. for 12 h. The mixture was diluted (DCM), washed (H20), dried (phase separator andconcentrated. The residue was purified by prep HPEC toyield the desired product (Compound B).

Reference： [1]Patent: US2015/203455,2015,A1 .Location in patent: Paragraph 0540-0543
[2]Patent: WO2015/110378,2015,A1 .Location in patent: Paragraph 00316; 00317; 00318
[3]Patent: US9440929,2016,B2 .Location in patent: Page/Page column 124

25
[ 64-18-6 ]
[ 302800-13-1 ]
[ 53484-16-5 ]

Yield	Reaction Conditions	Operation in experiment
98%	With iron; ammonium chloride; In isopropyl alcohol; for 24h;Reflux;	[0444j Step B: Preparation of 6-bromo-1-methyl-benzimidazole: A mixture of 5- bromo-N-methyl-2-nitro-aniline (6.0 g, 26 mmol), iron powder (14.5 g, 260 mmol), ammonium chloride (13.9 g, 260 mmol) and formic acid (49.0 mL, 1298 mmol) in 2- propanol (75 mL) was stirred under reflux for 24 hours. After cooling to ambient temperature, ethyl acetate (50 mL) was added. The solid was removed by filtering through a pad of celite. The filtrate was concentrated. Saturated sodium bicarbonate (20 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by flash chromatography on silica gel 10:1 ethyl acetate/MeOH to give 6-bromo-1-methyl-benzimidazole (5.35 g, 98percent) as solid.

Reference： [1]Patent: WO2015/175845,2015,A1 .Location in patent: Paragraph 0444

26
[ 342-23-4 ]
[ 53484-16-5 ]
(6-bromo-1-methyl-benzimidazol-2-yl)-bis(2-fluorophenyl)methanol [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	With lithium hexamethyldisilazane; In tetrahydrofuran; at -45℃; for 1h;	[0445j Step C: Preparation of (6-bromo- 1 -methyl-benzimidazol-2-yl)-bis(2- fluorophenyl)methanol: To a solution of bis(2-fluorophenyl)methanone (3.98 g, 18.2 mmol) and lithium bis(trimethylsilyl)amide (20.7 mL, 20.7 mmol) in THF (50 ml) was added 6- bromo-1-methyl-benzimidazole (3.5 g, 16.6 mmol) in THF (40 mL) dropwise at -45 °C. After the addition, the mixture was stirred at -45 °C for 1 hour. Aqueous saturated ammonium chloride solution (50 mL) and ethyl acetate (50 mL) were added. The organic layer was separated, washed with brine, dried (sodium sulfate), filtered and concentrated. The residue was purified by flash chromatography on silica gel using 2:1 hexane/ethyl acetate to give (6- bromo- 1 -methyl-benzimidazol-2-yl)-bis(2-fluorophenyl)methanol (6.32 g, 89percent) as solid.

Reference： [1]Patent: WO2015/175845,2015,A1 .Location in patent: Paragraph 0445

27
[ 53484-16-5 ]
2-[bis(2-fluorophenyl)-hydroxy-methyl]-3-methyl-benzimidazole-5-sulfonamide [ No CAS ]

Reference： [1]Patent: WO2015/175845,2015,A1

28
[ 53484-16-5 ]
S-[2-[bis(2-fluorophenyl)-hydroxy-methyl]-3-methyl-benzimidazol-5-yl]ethanethioate [ No CAS ]

Reference： [1]Patent: WO2015/175845,2015,A1

29
[ 53484-16-5 ]
2-[bis(2-fluorophenyl)-hydroxy-methyl]-3-methyl-benzimidazole-5-sulfonyl chloride [ No CAS ]

Reference： [1]Patent: WO2015/175845,2015,A1

30
[ 53484-16-5 ]
2-(1-methyl-1H-benzo[d]imidazol-6-yl)acetic acid [ No CAS ]

Reference： [1]Patent: WO2015/186056,2015,A1
[2]Journal of Medicinal Chemistry,2017,vol. 60,p. 9769 - 9789

31
[ 321745-86-2 ]
[ 53484-16-5 ]
tert-butyl 2-(1-methyl-1H-benzo[d]imidazol-6-yl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tris-(dibenzylideneacetone)dipalladium(0); monophosphine 1,2,3,4,5-pentaphenyl-1'-(di-tert-butylphosphino)ferrocene; In tetrahydrofuran; diethyl ether; at 20℃; for 1h;	Prepared according to general procedure 6 from 6- bromo-1-methyl-1 H-benzo[d]imidazole (490 mg, 2.32 mmol), (2-(tert-butoxy)-2-oxoethyl)zinc(ll) chloride (0.5M in Et20, 5.10 mL, 2.55 mmol), Pd2(dba)3 (106 mg, 0.1 16 mmol) and Q-Phos (167 mg, 0.232 mmol) in dioxane (4 mL). The reaction is complete after 1 h at rt. Purification of the crude by automated FC (Biichi, EtOAc / heptane 1 :99? 3:97? 5:95? 8:92? 15:85, 10 g silicagel, flow 10 mL/min) yields the title product. LC- MS: tR = 0.59 min, MH+ = 247.11 (conditions 3). General procedure 6 for a Negishi coupling. A sol. of bromoaryl / bromoheteroaryl, (2-(tert-butoxy)-2- oxoethyl)zinc(ll) chloride (0.5M in Et20), palladium catalyst, and optionally a ligand in THF is stirred between rt and 90 °C until the starting materials are consumed. The mixture is allowed to cool to rt, and the solvents are removed under reduced pressure. Chromatographic purification yields the desired compound.

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9769 - 9789
[2]Patent: WO2015/186056,2015,A1 .Location in patent: Page/Page column 98

32
[ 53484-16-5 ]
1-(3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenoxy)-3-(3-phenyl-6,7-dihydro-1H-pyrazolo[4,3-c]pyridin-5(4H)-yl)propan-2-ol [ No CAS ]

Reference： [1]Patent: WO2015/200677,2015,A2

33
[ 53484-16-5 ]
1-(7,8-dihydro-1,6-naphthyridin-6(5H)-yl)-3-(3-(1-methyl-1H-benzo[d]imidazol-6-yl)phenoxy)propan-2-ol [ No CAS ]

Reference： [1]Patent: WO2015/200677,2015,A2

34
[ 53484-16-5 ]
[ 26530-93-8 ]

Yield	Reaction Conditions	Operation in experiment
	With ammonium hydroxide; copper(l) chloride; at 100℃; for 5h;Sealed tube;	[0003901 To a stirred solution of compound 1 (0.2 g, 1 eq) in aq. ammonia solution (2 mL), copper chloride (catalytic amount) was added and heated at 100 °C for 5 h in a sealed tube. The progress of the reaction was monitored by TLC. After completion of the reaction, the reaction mixture was evaporated to dryness. The residue was stirred with 20percent methanol in dichloromethane and filtered. The filtrate was concentrated under reduced pressure to afford title compound 2. LCMS (mlz): 148.00 (M + 1).

Reference： [1]Patent: WO2016/57834,2016,A1 .Location in patent: Paragraph 000390

35
(2E)-3-(4-chloropyridin-3-yl)-N-(4-(N-morpholinylmethyl)phenyl)acrylamide [ No CAS ]
[ 76-05-1 ]
[ 53484-16-5 ]
(E)-3-(4-(1-methyl-1H-benzo[d]imidazol-6-yl)pyridin-3-yl)acrylic acid trifluoroacetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
95%		General procedure: A mixture of 13 (210 mg, 0.63 mmol), 5-bromothiazole (156 mg, 0.95 mmol), SPhos (26.0 mg, 0.06 mmol), SPhos-Pd-G2 (45.7 mg, 0.06 mmol) and 2 M aq. Cs2CO3 solution (0.793 ml, 1.59 mmol) in DME (4 mL) was heated at 130 °C for 1 h under microwave irradiation. The mixture was diluted with EtOAc (10 mL), dried over MgSO4, and solvent removed under vacuum. The residue was purified by column chromatography (NH silica gel, eluted with 5?17percent EtOAc/hexane) to yield (E)-tert-butyl 3-(4-(thiazol-5-yl)pyridin-3-yl)acrylate (14a tBu ester, 102 mg, 56percent) as a pale yellow solid. This compound was dissolved in TFA (2.0 ml) and stirred at rt for 2 h. After removal of solvent under reduced pressure, the residue was triturated with EtOAc/hexane (1:1) (3 mL) and the resulting precipitate collected by filtation to yield 14a TFA salt (79 mg, 36percent overall) as a colorless solid

Reference： [1]Bioorganic and Medicinal Chemistry,2017,vol. 25,p. 3018 - 3033

36
(R)-4H-1‘-azaspiro[isoxazole-5,3‘-bicyclo[2.2.2]octan]-3-amine [ No CAS ]
[ 53484-16-5 ]
(R)-N-(1-methyl-1H-benzo[d]imidazol-6-yl)-4H-1‘-azaspiro[isoxazole-5,3‘-bicyclo[2.2.2]octan]-3-amine hydrochloride [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
17%		j00672j To a solution of 6-bromo-1-methyl-1H-benzo[djimidazole (0.18 g, 0.83 mmol), compound (R)-A-2 (0.15 g, 0.83 mmol), tris(dibenzylideneacetone)dipalladium(0) (76 mg, 0.083 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (96 mg, 0.17 mmol) in dioxane (10 mL) under nitrogen at room temperature was added cesium carbonate (0.54 g, 1.7 mmol). The reaction mixture was stirred at 100 °C for 16 hours, then filtered and concentrated in vacuo. The residue was purified by prep-HPLC [Instrument: GX-E; Column: Phenomenex Gemini C18 250x50 mm, particle size: 10 .im; Mobile phase: 15-45percent acetonitrile in H20 (add 0.05percent NH3 H20, v/v)j. The combined fractions were lyophilized, treated with 0.2 M hydrochloric acid and again lyophilized to give:Compound (R)-57 (50 mg, 17percent yield) as a yellow solid: cSFC analytical (I) tR=3.545 mm., purity: 100.00percent; LCMS (FF): tR=1.630 mi, (ES+) mlz (M+H)+ =3 12.1; 1H-NMR(CD3OD, 400 MHz): 9.28 (s, 1H), 8.22 (d, J=1.6 Hz, 1H), 7.75 (d, J=8.8 Hz, 1H), 7.49 (dd, J19.2 Hz, J22.0 Hz, 1H), 4.11 (s, 3H), 3.74 (dd, J1=14 Hz, J2=2.0 Hz, 1H), 3.64 (d, J=14 Hz, 1H), 3.55-3.37 (m, 6H),2.46-2.41 (m, 2H), 2.16-2.12 (m, 1H), 2.05-1.95 (m, 2H).

Reference： [1]Patent: WO2017/69980,2017,A1 .Location in patent: Paragraph 00671; 00672

37
[ 53484-16-5 ]
N-(1-(3,4-difluorobenzyl)-1H-pyrazol-3-yl)-2-(1-methyl-1H-benzo[d]imidazol-6-yl)acetamide [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2017,vol. 60,p. 9769 - 9789

38
[ 942919-26-8 ]
[ 53484-16-5 ]
1-methyl-6-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-benzo[d]imidazole [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2018,vol. 61,p. 4386 - 4396

39
[ 4887-88-1 ]
[ 74-88-4 ]
[ 53484-15-4 ]
[ 53484-16-5 ]

Reference： [1]Journal of Organic Chemistry,2018,vol. 83,p. 6334 - 6353

40
1-[(4-methoxyphenyl)methyl]-1H-pyrazolo[4,3-b]pyridin-3-amine [ No CAS ]
[ 53484-16-5 ]
C₁₄H₁₂N₆ [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2018,vol. 28,p. 2641 - 2646

41
[ 401-55-8 ]
[ 53484-16-5 ]
ethyl 2-(5-bromo-3-methyl-2-thioxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)-2-fluoroacetate [ No CAS ]

Reference： [1]Advanced Synthesis and Catalysis,2018,vol. 360,p. 4795 - 4806

42
[ 53484-16-5 ]
6-ethynyl-1-methyl-1H-benzo[d]imidazole [ No CAS ]

Reference： [1]Patent: WO2019/13703,2019,A1

43
[ 53484-16-5 ]
(4-(3-((1-methyl-1H-benzo[d]imidazol-6-yl)ethynyl)imidazo[1,2-a]pyridin-6-yl)phenyl)(morpholino)methanone [ No CAS ]

Reference： [1]Patent: WO2019/13703,2019,A1

44
[ 1066-54-2 ]
[ 53484-16-5 ]
1-methyl-6-((trimethylsilyl)ethynyl)-1H-benzo[d]imidazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
38.3%	With copper(l) iodide; trans-bis(triphenylphosphine)palladium dichloride; phosphoric acid triphenyl ester; triethylamine; In tetrahydrofuran; for 16h;Reflux;	A mixture of 6-bromo-1-methyl-1H-benzo[djimidazole 5 (20 g, 94.75 mmol), trimethyl acetylene (28 mL, 285.7 mmol), CuT (2.7 g, 14.28 mmol), TPP (1.25 g, 4.76 mmol), TEA (40 mL, 285.6 mmol) and Pd(PPh3)C12 (3.3 g, 4.76 mmol) in THF (200 mL) was heated to reflux for 16 h. The reaction mixture was concentrated under reduced pressure and the residue was purified by column chromatography (silica gel, eluent pet-ether/EtOAc 80:20) to give 1- methyl-6-((trimethylsilyl)ethynyl)- 1H-benzo [di imidazole (10 g, 36.34 mmol, LC-MS 83percent, 38.3percent) as a brown solid. ?H NMR (400 MHz, CDC13) (ppm): 7.88 (s, 1H), 7.70 (d, J = 8.4 Hz, 1H), 7.54 (s, 1H), 7.39 (dd, J= 0.8 Hz, 8.4 Hz, 1H), 3.82 (s, 3H), 0.27 (s, 9H); MS (ESI) m/z 229.3 [C,3H,6N2Si+Hjt

Reference： [1]Patent: WO2019/13703,2019,A1 .Location in patent: Page/Page column 49; 50; 51

45
[ 79-31-2 ]
[ 53484-16-5 ]
[ 1447911-34-3 ]

Reference： [1]Organic Letters,2019

46
8-(4-chlorophenyl)-2-(2,2,2-trifluoroethylamino)-1,6-naphthyridin-7(6H)-one [ No CAS ]
[ 53484-16-5 ]
8-(4-chlorophenyl)-6-(1-methyl-1H-benzo[d]imidazol-6-yl)-2-(2,2,2-trifluoroethylamino)-1,6-naphthyridin-7(6H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; cesium fluoride; cis-N,N'-dimethyl-1,2-diaminocyclohexane; In acetonitrile; at 100℃; for 3h;Inert atmosphere;	A mixture of 8-(4-chlorophenyl)-2-(2,2,2-trifluoroethylamino)- l,6-naphthyridin-7(6f/)-one (50.0 mg, 0.14 mmol, 1.0 equiv.), Cul (26.6 mg, 0.14 mmol, 1.0 equiv.), CsF (63.8 mg, 0.4 mmol, 3.0 equiv.), N1N2- dimethylcy cl ohexane-l, 2-diamine (29.8 mg, 0.2 mmol, 1.5 equiv.), and 6- bromo-l -methyl- li7-benzo[

Reference： [1]Patent: WO2019/191470,2019,A1 .Location in patent: Paragraph 00729; 00734; 00735; 00736

47
8-(4-(difluoromethoxy)phenyl)-2-((2,2,2-trifluoroethyl)amino)pyrido[4,3-d]pyrimidin-7(6H)-one [ No CAS ]
[ 53484-16-5 ]
8-(4-(difluoromethoxy)phenyl)-6-(1-methyl-1H-benzo[d]imidazol-6-yl)-2-((2,2,2-trifluoroethyl)amino)pyrido[4,3-d]pyrimidin-7(6H)-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With copper(l) iodide; cesium fluoride; cis-N,N'-dimethyl-1,2-diaminocyclohexane; In 1,4-dioxane; at 100℃; for 16h;Inert atmosphere;	General procedure: A mixture of 8-(4-chlorophenyl)-2-((2,2,2- trifluoroethyl)amino)pyrido[4,3-i/]pyrimi-din-7(d7/)-one (100 mg, 0.28 mmol, 1.0 equiv), 5-bromo-2-methyl-2H-indazole (119 mg, 0.56 mmol, 2.0 equiv.), Cul (5.4 mg, 0.028 mmol, 0.1 equiv.), N1, A2-dimethylcy cl ohexane-l, 2-diamine (8.1 mg, 0.056 mmol, 0.2 equiv.), CS2CO3 (276 mg, 0.847 mmol, 3.0 equiv.) and dioxane (2 mL) was stirred at l00C under N2 atmosphere for l6h. The crude mixture was concentrated under reduced pressure, and the resulting residue was purified by flash column chromatography on silica gel to yield 8-(4- chlorophenyl)-6-(2-methyl-2H-indazol-5-yl)-2-((2,2,2- tri fl uoroethyl )am i no)py ri do[-/, 3-6/]pyrimidin-7(6//)-one (Example 123).

Reference： [1]Patent: WO2019/191470,2019,A1 .Location in patent: Paragraph 00270; 00280; 00281; 00367; 00368; 00369

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P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
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.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
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

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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. 53484-16-5 ] {[proInfo.proName]}

Quality Control of [ 53484-16-5 ]

Related Doc. of [ 53484-16-5 ]

Product Details of [ 53484-16-5 ]

Safety of [ 53484-16-5 ]

Application In Synthesis of [ 53484-16-5 ]

[ 53484-16-5 ] Synthesis Path-Upstream 1~8

[ 53484-16-5 ] Synthesis Path-Downstream 1~47

Related Functional Groups of [ 53484-16-5 ]

Bromides

Related Parent Nucleus of [ 53484-16-5 ]

Benzimidazoles

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 53484-16-5 ]

Related Parent Nucleus of
[ 53484-16-5 ]