[ CAS No. 952511-48-7 ]

Name: 5-Bromo-4-methyl-1H-benzo[d]imidazole
Brand: Ambeed
SKU: A239929
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Quality Control of [ 952511-48-7 ]

COA GC NMR CNMR HPLC/UPLC LC-MS

Related Doc. of [ 952511-48-7 ]

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Product Details of [ 952511-48-7 ]

CAS No. :	952511-48-7	MDL No. :	MFCD18642426
Formula :	C₈H₇BrN₂	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	211.06	Pubchem ID :	59214444
Synonyms :

Computed Properties of [ 952511-48-7 ]

TPSA :Topological Polar Surface Area	28.7	H-Bond Acceptor Count :	1
XLogP3 :	2.5	H-Bond Donor Count :	1
SP3 :	0.13	Rotatable Bond Count :	0

Safety of [ 952511-48-7 ]

Signal Word:	Warning	Class	N/A
Precautionary Statements:	P261-P280-P305 P351 P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H332-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 952511-48-7 ]

Upstream synthesis route of [ 952511-48-7 ]
Downstream synthetic route of [ 952511-48-7 ]

[ 952511-48-7 ] Synthesis Path-Upstream 1~5

1
[ 64-18-6 ]
[ 952511-74-9 ]
[ 952511-48-7 ]

Yield	Reaction Conditions	Operation in experiment
98%	at 60℃; for 12.00 h;	3: A mixture of 156 (28 g,140 mmol), formic acid (240 mL) and 37percent> concentrated HC1 (400 mL) was heated to 60 °C for 12 h, cooled in an ice-water bath, and the pH slowly adjusted to 8-9 with 28percent> concentrated NH4OH. The solid was collected by filtration, washed with water and dried in air to afford 25 g (98percent) of 5-bromo-4-methyl-lH-benzo[d]imidazole (158) as a yellow solid: MS (ESI) m/z = 213 [M+l]+.

Reference： [1] Patent: WO2013/26914, 2013, A1. Location in patent: Page/Page column 143
[2] Patent: US2010/222345, 2010, A1. Location in patent: Page/Page column 87

2
[ 122-51-0 ]
[ 290353-57-0 ]
[ 952511-48-7 ]

Yield	Reaction Conditions	Operation in experiment
73%	Stage #1: at 50℃; for 2.00 h; Stage #2: at 20 - 70℃; for 0.50 h;	To a stirred solution of 1-bromo-2-methyl-3,4-dinitro-benzene (Tetrahedron Lett. 2000, 41(22), 4277-4279) (2.61 g, 10 mmol) in EtOH (50 mL) was added SnCl₂(1.89 g, 100 mmol). The mixture was stirred at 50° C. for 2 h. The mixture was cooled to rt, and triethylorthoformate (25 mL) was added. After heating for 30 min at 70° C., the mixture was cooled to rt, diluted with satd. aq. NaHCO₃(100 mL), and extracted with EtOAc (3.x.60 mL). The combined organic layers were washed with satd. aq. NaCl (100 mL), dried, and concentrated to give a solid residue. The residue was stirred vigorously with MeOH (100 mL) and the precipitate removed by filtration. The filtrate was concentrated to yield the crude product which was then purified by FCC (EtOAc/hexanes) to give 1.55 g (73percent) of the desired product. MS: mass calcd. for C₈H₇BrN₂, 209.98; m/z found, 211.0 [M+H]⁺. ¹H NMR (CD₃OD): 8.18 (s, 1H), 7.41 (d, J=8.7 Hz, 1H), 7.34 (d, J=8.6 Hz, 1H), 2.61 (s, 3H).

Reference： [1] Patent: US2009/156613, 2009, A1. Location in patent: Page/Page column 22

3
[ 55289-35-5 ]
[ 952511-48-7 ]

Reference： [1] Patent: WO2013/26914, 2013, A1
[2] Biochemical and Biophysical Research Communications, 2015, vol. 456, # 1, p. 282 - 287

4
[ 290353-57-0 ]
[ 952511-48-7 ]

Reference： [1] Patent: WO2013/26914, 2013, A1

5
[ 64-18-6 ]
[ 952511-48-7 ]

Reference： [1] Biochemical and Biophysical Research Communications, 2015, vol. 456, # 1, p. 282 - 287

[ 952511-48-7 ] Synthesis Path-Downstream 1~10

1
[ 952511-48-7 ]
tert-butyl (2R,3S)-2-(3-bromopropyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate [ No CAS ]
tert-butyl (2R,3S)-2-(3-(5-bromo-4-methyl-1H-benzo[d]imidazol-1-yl)propyl)-3-((tert-butyldimethylsilyl)oxy)piperidin-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 4h;	Tert-butyl (2R,3S)-2-(3-bromopropyl)-3-((tert-butyldimemylsilyl)oxy)piperidine-l- carboxylate (40 mg, 0.09 mmol) obtained from Step 1-5 of Example 1 was dissolved in N,N- dimethylformamide (2 niL, 0.05 M). Then, potassium carbonate (25 mg, 0.18 mmol) and 5- bromo-4-methyl-lH-benzo[d]imidazole (18 mg, 0.09 mmol) were added thereto, and the mixture was stirred at room temperature for 4 hours. When the reaction was completed, the solvent was removed, and the resulting mixture was diluted with ethyl acetate and washed with saturated sodium chloride solution. The organic layer was collected, dried over sodium sulfate, filtered and concentrated under reduced pressure, and then purified by column chromatography (hexane: ethyl acetate = 1 : 1) to give the title compound (43 mg, yield: 85percent).

Reference： [1]Patent: WO2018/147626,2018,A1.Location in patent: Page/Page column 51; 52

2
[ 952511-48-7 ]
1-(5-(3-fluorophenyl)-4-methyl-1H-benzo[d]imidazol-1-yl)-3-((2R,3S)-3-hydroxypiperidin-2-yl)propane-2-one [ No CAS ]

Reference： [1]Patent: WO2016/200116,2016,A1

3
[ 952511-48-7 ]
benzyl (2R,3S)-3-((tert-butyldimethylsilyl)oxy)-2-(3-(5-(3-fluorophenyl)-4-methyl-1H-benzo[d]imidazol-1-yl)-2-oxopropyl)piperidine-1-carboxlate [ No CAS ]

Reference： [1]Patent: WO2016/200116,2016,A1

4
[ 952511-48-7 ]
benzyl (2R,3S)-2-(3-bromo-2-oxopropyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate [ No CAS ]
benzyl (2R,3S)-2-(3-(5-bromo-4-methyl-1H-benzo[d]imidazol-1-yl)-2-oxopropyl)-3-((tert-butyldimethylsilyl)oxy)piperidine-1-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 3h;	5-Bromo-4-methyl-lH-benzo[d]imidazole (86.53 mg, 0.41 mmol) was dissolved in N,N-dimethylformamide (2 mL, 0.20 M) to which potassium carbonate (114.09 mg, 0.83 mmol) was added and then stirred at room temperature for 10 minutes. Then, benzyl (2R,3S)-2- (3 -bromo-2-oxopropyl)-3-((tert-butyldimemylsilyl)oxy)piperidine-l -carboxylate (200 mg, 0.41 mmol) was added thereto and stirred at room temperature for 3 hours. When the reaction was completed, the solvent was removed and the resulting mixture was diluted with ethyl acetate and washed with saturated sodium chloride solution. The organic layer was collected, dried over magnesium sulfate, filtered and concentrated under reduced pressure, and then purified by column chromatography (hexane:ethylacetate = 5:1) to give the title compound (217 mg, yield: '86percent)

Reference： [1]Patent: WO2016/200116,2016,A1.Location in patent: Page/Page column 35

5
[ 64-18-6 ]
2-bromo-5,6-diaminotoluene dihydrochloride [ No CAS ]
[ 952511-48-7 ]