952511-48-75-broMo-4-Methyl-1H-benzo[d]iMidazole

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]+.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 SnClTert-butyl (2R, 3S)-2-(3-bromopropyl)-3-((tert-butyldimemylsilyl)oxy)piperidine-l- carboxylate (40 mg, 0.09 mmol) obtained from Step 1-5 of 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).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)

Molecular Weight:211.06
XLogP3:2.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:209.97926
Monoisotopic Mass:209.97926
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes