Trifluoroacetic anhydride → 1-(5-Bromopyridin-2-yl)-5-methoxy-2-(trifluoromethyl)-1H-benzimidazole
Reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=2[NH:17][C:18](=O)[C:19]([F:22])([F:21])[F:20])=[N:6][CH:7]=1.O(C(C(F)(F)F)=O)C(C(F)(F)F)=O>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:9]3[CH:14]=[CH:13][C:12]([O:15][CH3:16])=[CH:11][C:10]=3[N:17]=[C:18]2[C:19]([F:22])([F:21])[F:20])=[N:6][CH:7]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of N-[2-(5-Bromo-pyridin-2-ylamino)-5-methoxy-phenyl]-2,2,2-trifluoro-acetamide (70 mg, 0.18 mmol) in toluene (15 mL) was added (CF3CO)2O (6 mL). The resulting solution was allowed to stir overnight at reflux. The volatile components were then removed under reduced pressure and the residue was purified by SGC using 1:7 EtOAc/petroleum ether as eluents to provide 5 mg (6%) of 1-(5-Bromo-pyridin-2-yl)-5-methoxy-2-trifluoromethyl-1H-benzoimidazole (cc) as a white solid. 1HNMR (400 MHz, DMSO-D6) δ 3.84 (3H, s), 7.11-7.13 (1H, d), 7.37 (1H, d), 7.45 (1H, s), 7.81 (1H, d), 8.46 (1H, d), 8.88 (1H, s) ppm.