Br[C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]([F:22])([F:21])[F:20])=[N:6][CH:7]=1.[NH:23]1CCC[C@H:24]1[C:25](O)=O.CCN.C([O-])([O-])=O.[K+].[K+]>O.[Cu]I.CS(C)=O>[CH2:24]([NH:23][C:2]1[CH:7]=[N:6][C:5]([N:8]2[C:12]3[CH:13]=[CH:14][C:15]([O:17][CH3:18])=[CH:16][C:11]=3[N:10]=[C:9]2[C:19]([F:22])([F:21])[F:20])=[CH:4][CH:3]=1)[CH3:25]Into a 10 ml sealed tube, was placed 1-(5-Bromo-pyridin-2-yl)-5-methoxy-2-trifluoromethyl-1H-benzoimidazole (30 g, 80.65 mmol). To this was added CuI (20 mg), L-Proline (20 g), CH3CH2NH2 (2 ml) and K2CO3 (30 g) followed by the addition of dimethylsulfoxide (DMSO) (6 ml). The resulting solution was allowed to stir for 6 hours at 60° C., then diluted with 10 ml of H2O and extracted two times with 30 ml of EtOAc. Organic layers were combined and washed with 20 ml of H2O. The combined organic layer was dried and concentrated, and the residue was purified by SGC using 1:12-1:6 EtOAc/petroleum ether as eluent to provide 21 g (78%) of Ethyl-[6-(5-methoxy-2-trifluoromethyl-benzoimidazol-1-yl)-pyridin-3-yl]-amine (Compound 162) as a white solid.
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