[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:13]=3[CH3:22])[C:6]=2[CH:5]=[C:4]([N+:23]([O-])=O)[CH:3]=1.O.O.[Sn](Cl)Cl.Cl>CO>[Br:1][C:2]1[C:10]2[N:9]=[CH:8][N:7]([CH2:11][C:12]3[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:20])([F:19])[F:21])[C:13]=3[CH3:22])[C:6]=2[CH:5]=[C:4]([NH2:23])[CH:3]=1To a solution of 4-bromo-1-(2-methyl-3-(trifluoromethyl)benzyl)-6-nitro-1H-benzo[d]imidazole (2.5 g, 6.04 mmol) in Methanol (30 mL) in a 250 ml round bottomed flask was added Tin(II)chloride dihydrate (8.17 g, 36.2 mmol) and HCl (1.65 mL, 54.3 mmol). The reaction mixture was left to stir at 80° C. for 1 h. The solvent was removed and diluted with water (100 mL) and this solution was decanted into a 250 mL Erlenmeyer flask. The brown residue in the round bottomed flask was dissolved in 100 mL of EtOAc and washed with 1N NaOH, brine, dried and evaporated to yield a brown solid. The water layer was extracted with EtOAc, washed with 1N NaOH, brine, dried (MgSO4) and evaporated to a brown solid. The solids found to be identical by 1 cms and were combined to yield 4-bromo-1-(2-methyl-3-(trifluoromethyl)benzyl)-1H-benzo[d]imidazol-6-amine (2.28 g, 5.93 mmol, 98% yield). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.44 (s, 3H) 5.24 (s, 2H) 6.39 (d, J=2.02 Hz, 1H) 6.87 (d, J=8.08 Hz, 1H) 6.92 (d, J=2.02 Hz, 1H) 7.21 (t, J=7.83 Hz, 1H) 7.62 (d, J=7.83 Hz, 1H) 7.69 (s, 1H); LC/MS: MS (ES+) m/e 385 [M+H]+.
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