Potassium Carbonate → 5-[5-Methoxy-2-(trifluoromethyl)-1H-benzimidazol-1-yl]pyridin-2-amine

HRID 1696724Notes

Reaction equation

FC(F)(F)C([NH:5][C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:16]3[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[CH:20][C:15]=3[N:14]=[C:13]2[C:23]([F:26])([F:25])[F:24])=[CH:8][N:7]=1)=O.C([O-])([O-])=O.[K+].[K+]>CO>[CH3:22][O:21][C:19]1[CH:18]=[CH:17][C:16]2[N:12]([C:9]3[CH:10]=[CH:11][C:6]([NH2:5])=[N:7][CH:8]=3)[C:13]([C:23]([F:26])([F:24])[F:25])=[N:14][C:15]=2[CH:20]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 2,2,2-Trifluoro-N-[5-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyridin-2-yl]-acetamide (100 mg, 0.25 mmol) in methanol (20 ml) was added K2CO3 (510 mg, 3.69 mmol). The resultant solution was allowed to stir overnight at 65° C. The reaction progress was monitored by LCMS. After completion, the reaction mixture was quenched by adding 30 ml of H2O. The resultant solution was extracted three times with 30 ml of EtOAc and the organic layers were combined and dried over Na2SO4. After removal of the drying reagent and the solvent, the residue was purified by SGC using 1:3 EtOAc/petroleum ether as eluents to provide 80 mg (79%) of 5-(5-Methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyridin-2-ylamine (gg) as a white solid. 1NMR (400 MHz, CDCl3) δ 8.11 (1H, s), 7.49 (1H, dd, J=2.16 Hz), 7.47 (1H, dd, J=2.16 Hz), 7.33 (1H, dd, J=8.8 Hz), 7.04 (1H, s), 6.69 (1H, dd, J=8.8 Hz), 5.08 (2H, s), 3.87 (3H, s) ppm.

Workup

customAfter completion, the reaction mixture was quenched
additionby adding 30 ml of H2O
extractionThe resultant solution was extracted three times with 30 ml of EtOAc
dry with materialdried over Na2SO4
customAfter removal of the drying reagent
customthe solvent, the residue was purified by SGC

Sources & evidence

ORD record: ord-b1e0d709001e4cf48ad850ab55849612
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163777B2

Reaction notes

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