Trifluoroacetic anhydride → 1-(5-Bromopyridin-2-yl)-5-methoxy-2-(trifluoromethyl)-1H-benzimidazole

HRID 1696720Notes

Reaction equation

HRID 1696720 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]=1

Participants

4

Reactant 2

HCID 9845Trifluoroacetic anhydrideHCID 59004198HCID 59004198, compound

Product 1

HCID 573569051-(5-Bromopyridin-2-yl)-5-methoxy-2-(trifluoromethyl)-1H-benzimidazoleYield 7.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

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.

Workup

  1. temperatureat reflux
  2. customThe volatile components were then removed under reduced pressure
  3. customthe residue was purified by SGC

Sources & evidence

ORD record
ord-ef21e8658d5841b2bdc7783cd594b0cf
Source dataset
uspto-grants-2012_04
Patent number
US08163777B2

Reaction notes

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