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Quality Control of [ 942590-05-8 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

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Product Details of [ 942590-05-8 ]

CAS No. :	942590-05-8	MDL No. :	MFCD13182500
Formula :	C₁₂H₁₃BrN₂O₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	297.15	Pubchem ID :	-
Synonyms :

Safety of [ 942590-05-8 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501	UN#:
Hazard Statements:	H302-H312-H315-H319-H332-H335	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 942590-05-8 ]

* 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 [ 942590-05-8 ]
Downstream synthetic route of [ 942590-05-8 ]

[ 942590-05-8 ] Synthesis Path-Upstream 1~1

1
[ 942590-05-8 ]
[ 73183-34-3 ]
[ 1021918-86-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium acetate; triethylamine In 1,4-dioxane at 110℃;	A mixture of 1 , 1 -dimethylethyl 5-bromo-lH-benzimidazole-l -carboxylate (10.2 mmol), bis(pinacolato)diboron (11.2 mmol), palladium(II) acetate (1.02 mmol), dichloro[l,l '-bis(diphenylphosphino)ferrocene]palladium(II) (1.02 mmol), and potassium acetate (30.4 mmol) in triethylamine (2 mL) and 1,4-dioxane (50 mL) was heated at 110 °C overnight. The reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (10percent ethyl acetate/petroleum ether) to afford the title product as a solid (42percent).
1.47 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; triethylamine In 1,4-dioxane at 110℃; Inert atmosphere	1 ,1 -Dimethylethyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzimidazole-1 - carboxylateTo a solution of 1 , 1 -dimethylethyl 5-bromo-1 /-/-benzimidazole-1 -carboxylate (3.02 g) in 1 ,4- dioxane (50 mL) were added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1 ,3,2-dioxaborolane (2.837 g), potassium acetate (7.978 g) and TEA (2 mL). Pd(OAc)₂ (227 mg) and Pd(dppf)CI₂ (743 mg) were added under nitrogen and the reaction mixture was stirred under reflux (1 10 °C) overnight. The reaction mixture was washed with water three times and with saturated brine and dried over sodium sulfate. Solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography (petroleum ether / EtOAc 8:1 ) to afford 1.47 g of the titled compound.

Reference： [1] Patent: WO2011/66211, 2011, A1, . Location in patent: Page/Page column 71
[2] Patent: WO2009/7751, 2009, A2, . Location in patent: Page/Page column 120-121
[3] Patent: WO2008/51493, 2008, A2, . Location in patent: Page/Page column 151
[4] Bioorganic and Medicinal Chemistry Letters, 2011, vol. 21, # 22, p. 6793 - 6799
[5] Patent: WO2013/28445, 2013, A1, . Location in patent: Page/Page column 56; 57

[ 942590-05-8 ] Synthesis Path-Downstream 1~4

1
[ 24424-99-5 ]
[ 4887-88-1 ]
[ 942590-05-8 ]

Yield	Reaction Conditions	Operation in experiment
98%	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 4h;	To a solution of above prepared 5-bromo-lH-benzo[d]imidazole (3.25 g, 22.1 mmol) in THF (65 mL) was added Boc20 (5.79 g, 26.5 mmol), Et3N (3.35, 33.15 mmol) and DMAP (270 mg, 2.21 mmol). The mixture was stirred at room temperature for 4 h, diluted with water (200 mL), extracted with ethyl acetate (200 mL). The organic layer was washed with water (2 x 100 mL) and brine (100 mL), dried over Na2S04, concentrated to give 0601-187 (4.8 g, 98%) as a oil. LCMS: 241 [M-55]+. 1H NMR (400 MHz, DMSO-<¾) delta 1.65 (s, 9H), 7.57 (dd, J; = 8.4 Hz, J2 = 20 Hz, 1H), 7.73 (d, J= 8.4 Hz, 1H), 7.88 (d, J = 9.2 Hz, 1H), 8.03 (d, J= 35.6 Hz, 1H), 8.70 (d, J= 8.0 Hz, 1H).
98%	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 4h;	To a solution of above prepared <strong>[4887-88-1]5-bromo-1H-benzo[d]imidazole</strong> (3.25 g, 22.1 mmol) in THF (65 mL) was added Boc2O (5.79 g, 26.5 mmol), Et3N (3.35, 33.15 mmol) and DMAP (270 mg, 2.21 mmol). The mixture was stirred at room temperature for 4 h, diluted with water (200 mL), extracted with ethyl acetate (200 mL). The organic layer was washed with water (2×100 mL) and brine (100 mL), dried over Na2SO4, concentrated to give 0601-187 (4.8 g, 98%) as a oil. LCMS: 241 [M-55]+. 1H NMR (400 MHz, DMSO-d6) delta 1.65 (s, 9H), 7.57 (dd, J1=8.4 Hz, J2=20 Hz, 1H), 7.73 (d, J=8.4 Hz, 1H), 7.88 (d, J=9.2 Hz, 1H), 8.03 (d, J=35.6 Hz, 1H), 8.70 (d, J=8.0 Hz, 1H).
98%	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 4h;	Prepared above 5-bromo -1H- benzo [d] imidazole (3.25g, 22.1mmol) in solution in THF (65 mL) of, Boc2O (5.79g, 26.5mmol), Et3N (3.35,33.15mmol) and DMAP (270mg, 2.21mmol) was added. The mixture was stirred for 4 hours at room temperature, then diluted with water (200mL), and extracted with ethyl acetate (200mL). The organic layer was washed with water (2 × 100 mL) and brine (100 mL), dried over Na2SO4, and concentrated to give 0601-187 as an oil (4.8g, 98%).

88%	With triethylamine; In tetrahydrofuran; at 25℃; for 18h;	[00512] A. tert-Butyl S-bromo-lH-benzofcphimidazole-l-carboxylate. 5-Bromo- l H-benzo[d] imidazole (0.300 g, 1.52 mmol), di-tert-butyl dicarbonate (0.397 g, 1.82 mmol), triethyl amine (0.307 g, 3.04 mmol) and tetrahydrofuran (10 mL) were stirred at 25 C for 18 h. The solution was condensed under reduced pressure and the product was isolated using Biotage silica gel chromatography (0-80% ethyl acetate in hexanes). Fractions containing product were concentrated to give (0.398 g, 88% yield). MS (ESI) m/z 298 [M+ 1]+.
88%	With triethylamine; In tetrahydrofuran; at 25℃; for 18h;	5-Bromo-1H-benzo[d]imidazole (0.300 g, 1.52 mmol), di-tert-butyl dicarbonate (0.397 g, 1.82 mmol), triethyl amine (0.307 g, 3.04 mmol) and tetrahydrofuran (10 mL) were stirred at 25 C for 18 h. The solution was condensed under reduced pressure and the product was isolated using silica gel chromatography (0-80% ethyl acetate in hexanes). Fractions containing product were concentrated to give (0.398 g, 88% yield).
	With dmap; In dichloromethane; at 20℃; for 20h;	To a suspension of <strong>[4887-88-1]5-bromo-1H-benzimidazole</strong> (830 mg), in DCM (100 mL) was added thethylamine (0.70 mL), DMAP (62 mg) and di-tert-butyl dicarbonate (1.11 g). The mixture was allowed to stir at room temperature for 20 h. The reaction mixture was washed with water, separated using a hydrophobic frit and was evaporated in vacuo. The crude material was purified by ISCO Companion silica chromatography, eluting with a gradient 15-50% EtOAc in cyclohexane to give the title compound. 1H NMR (CDCI3) delta 8.37 (1 H, s), 7.86 (1 H, d), 7.80 (1 H, d), 7.42 (1 H, dd), 1.66 (9H, s).
	With triethylamine; In dichloromethane; at 0 - 20℃;	To a 0 C solution of 5-bromo-lH-benzimidazole (10.2 mmol) in dichloromethane (30 mL) was dropwise added bis( 1,1 -dimethylethyl) dicarbonate (1 1.2 mmol) and triethylamine (15.2 mmol). The reaction mixture was then stirred at room temperature overnight. The mixture was washed with water (3 x 10 mL) and brine, then dried over sodium sulfate, filtered, and concentrated in vacuo to afford the crude product.

Reference： [1]Patent: WO2011/130628,2011,A1 .Location in patent: Page/Page column 229
[2]Patent: US2013/102595,2013,A1 .Location in patent: Paragraph 0582
[3]Patent: JP2015/187145,2015,A .Location in patent: Paragraph 0494
[4]Patent: WO2008/51493,2008,A2 .Location in patent: Page/Page column 151
[5]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6793 - 6799
[6]Patent: WO2007/71434,2007,A1 .Location in patent: Page/Page column 73
[7]Patent: WO2011/66211,2011,A1 .Location in patent: Page/Page column 70-71

2
[ 942590-05-8 ]
[ 73183-34-3 ]
[ 1021918-86-4 ]

Yield	Reaction Conditions	Operation in experiment
42%	With potassium acetate; triethylamine;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; In 1,4-dioxane; at 110℃;	A mixture of 1 , 1 -dimethylethyl 5-bromo-lH-benzimidazole-l -carboxylate (10.2 mmol), bis(pinacolato)diboron (11.2 mmol), palladium(II) acetate (1.02 mmol), dichloro[l,l '-bis(diphenylphosphino)ferrocene]palladium(II) (1.02 mmol), and potassium acetate (30.4 mmol) in triethylamine (2 mL) and 1,4-dioxane (50 mL) was heated at 110 C overnight. The reaction mixture was concentrated in vacuo and the residue purified by flash chromatography (10% ethyl acetate/petroleum ether) to afford the title product as a solid (42%).
	With potassium acetate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,4-dioxane; at 80℃; for 16h;	tert-Butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)benzoimidazole-l-carboxylateA mixture of tert-butyl 5 -bromobenzoimidazole- 1-carboxylate (2.5 g, 8.5 mmol), bispinacolatodiboran (2.56 g, 10.07 mmol), potassium acetate (3.3 g, 33.67 mmol) and 1,1'- <n="122"/>bis(diphenylphosphino)ferrocenedichloropalladium(II) dichloromethane adduct (200 mg) in dioxane (25 mL) was degassed several times then heated at 8O0C for 16 hours. The mixture was evaporated and dissolved in DCM, filtered and the filtrate chromatographed on silica, eluting with 20%ethyl acetate in hexane, to give the desired material as a pale yellow gum (2.65 g).LCMS Spectrum M(-BOC)H+ 245, retention time 1.90mins, method monitor base.
	With potassium acetate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In dichloromethane; dimethyl sulfoxide; at 100℃; for 18h;	[00513] B. tert-Butyl 5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH- benzo[d]imidazole-l-carboxylate. tert-Butyl 5 -bromo-lH-benzo[d] imidazole- 1- carboxylate (0.300 g, 1.01 mmol), bis(pinacolato)diboron (0.283 g, 1.1 1 mmol), [1,1'- bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with dichloromethane (1 : 1) (0.074 g, 0.09 mmol), potassium acetate (0.297 g, 3.03 mmol), dichloromethane (2mL) and methylsulfoxide (1 mL) were combined in a sealed tube and heated to 100 C for 18 h. The solution was condensed under reduced pressure and the product was used without purification in the next step (0.363 g). MS (ESI) m/z 345 [M+l]+.

		tert-Butyl 5-bromo-1H-benzo[d]imidazole-1-carboxylate (0.300 g, 1.01 mmol), bis(pinacolato)diboron (0.283 g, 1.11 mmol), [1,1'-bis(diphenylphosphino)ferrocene] dichloropalladium(II) complex with dichloromethane (1:1) (0.074 g, 0.09 mmol), potassium acetate (0.297 g, 3.03 mmol), dichloromethane (2mL) and methylsulfoxide (1 mL) were combined in a sealed tube and heated to 100 C for 18 h. The solution was condensed under reduced pressure and the product was used without purification in the next step (0.363 g).
1.47 g	With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; palladium diacetate; triethylamine; In 1,4-dioxane; at 110℃;Inert atmosphere;	1 ,1 -Dimethylethyl 5-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-benzimidazole-1 - carboxylateTo a solution of 1 , 1 -dimethylethyl 5-bromo-1 /-/-benzimidazole-1 -carboxylate (3.02 g) in 1 ,4- dioxane (50 mL) were added 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi-1 ,3,2-dioxaborolane (2.837 g), potassium acetate (7.978 g) and TEA (2 mL). Pd(OAc)2 (227 mg) and Pd(dppf)CI2 (743 mg) were added under nitrogen and the reaction mixture was stirred under reflux (1 10 C) overnight. The reaction mixture was washed with water three times and with saturated brine and dried over sodium sulfate. Solvent was removed under reduced pressure and the crude product was purified by silica gel column chromatography (petroleum ether / EtOAc 8:1 ) to afford 1.47 g of the titled compound.

Reference： [1]Patent: WO2011/66211,2011,A1 .Location in patent: Page/Page column 71
[2]Patent: WO2009/7751,2009,A2 .Location in patent: Page/Page column 120-121
[3]Patent: WO2008/51493,2008,A2 .Location in patent: Page/Page column 151
[4]Bioorganic and Medicinal Chemistry Letters,2011,vol. 21,p. 6793 - 6799
[5]Patent: WO2013/28445,2013,A1 .Location in patent: Page/Page column 56; 57

3
[ 24424-99-5 ]
[ 4887-88-1 ]
[ 942590-05-8 ]
[ 1006899-77-9 ]

Yield	Reaction Conditions	Operation in experiment
	With dmap; In tetrahydrofuran; for 16h;Heating / reflux;	tert-Butyl 5-bromobenzoimidazole- 1 -carboxylateA solution of 5-bromo-lH-benzoimidazole (2 g, 10.1 mmol), (2-methylpropan-2- yl)oxycarbonyl tert-butyl carbonate (3.3 g, 15.1 mmol) and DMAP (200 mg) in THF (30 mL) was heated at reflux for 16 hours. The reaction was allowed to cool, diluted with ethyl acetate and washed with water. The organics were dried (MgSO4), filtered and evaporated and the residue chromatographed on silica, eluting with 20% ethyl acetate in hexane, to give the desired material as a mixture of isomers (2.5 g). The material was used without further purification. LCMS Spectrum no MH+ ion observed, retention time 2.67mins, method monitor base.
	With triethylamine;dmap; In dichloromethane; at 20℃; for 0.5h;	To a solution of <strong>[4887-88-1]5-bromo-1H-benzimidazole</strong> (1.0 g, 5.1 mmol) in dichloromethane (25 mL) was added triethylamine (3.6 mL, 25.5 mmol) followed by di-t-butyldicarbonate (3.3 g, 15.2 mmol) and 4-(dimethylamino)-pyridine (cat). The reaction was stirred at room temperature for 30 min, then was quenched with H2O. The layers were separated and the aqueous extracted 2× CH2Cl2. The combined organics were dried (Na2SO4), concentrated in vacuo, and chromatographed (10-20% EtOAc/hexanes). This provided the product as the two Boc regioisomers which were separated and characterized but not assigned as to the specific regioisomer. The more polar isomer was used for the subsequent reactions.Isomer a (less polar): 1H NMR (400 MHz, CDCl3): delta-8.40 (s, 1H), 7.92 (s, 1H), 7.86 (d, 1H, J=8.5 Hz), 7.49 (d, 1H, J=8.5 Hz), 1.69 (s, 9H).Isomer b (more polar): 1H NMR (400 MHz, CDCl3): delta-8.38 (s, 1H), 8.18 (s, 1H), 7.63 (d, 1H, J=8.5 Hz), 7.46 (d, 1H, J=8.5 Hz), 1.69 (9H).

Reference： [1]Patent: WO2009/7751,2009,A2 .Location in patent: Page/Page column 121
[2]Patent: US2010/222345,2010,A1 .Location in patent: Page/Page column 43

4
[ 942590-05-8 ]
[ 1895006-01-5 ]
[ 2229831-36-9 ]

Yield	Reaction Conditions	Operation in experiment
75%	With dilithium tetrabromocuprate; 1,1,1,3,3,3-hexamethyl-2-(trimethylsilyl)-2-trisilanol; Ir(2-(2,4-difluorophenyl)-5-fluoropyridine)<SUB>2</SUB>(4,4'-di(trifluoromethyl)-2,2'-bipyridyl)PF<SUB>6</SUB>; sodium carbonate In acetone at 35℃; Irradiation;

Reference： [1]Le, Chip; Chen, Tiffany Q.; Liang, Tao; Zhang, Patricia; MacMillan, David W. C. [Science, 2018, vol. 360, # 6392, p. 1010 - 1014]

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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. 942590-05-8 ] {[proInfo.proName]}

Quality Control of [ 942590-05-8 ]

Related Doc. of [ 942590-05-8 ]

Product Details of [ 942590-05-8 ]

Safety of [ 942590-05-8 ]

Application In Synthesis of [ 942590-05-8 ]

[ 942590-05-8 ] Synthesis Path-Upstream 1~1

[ 942590-05-8 ] Synthesis Path-Downstream 1~4

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry