[H-].[Na+].[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][NH:12][C:13](=[O:15])[CH3:14])[CH:7]=[N:8][C:9]=1[Cl:10].I[CH3:17]>CN(C=O)C.CCOC(C)=O>[Cl:3][C:4]1[CH:5]=[C:6]([CH2:11][N:12]([CH3:17])[C:13](=[O:15])[CH3:14])[CH:7]=[N:8][C:9]=1[Cl:10]NaH (41 mg, 1.0 mmol, Aldrich, 60% dispersion in mineral oil) was added portionwise to a solution of N-(5,6-dichloro-pyridin-3-ylmethyl)-acetamide (150 mg, 0.68 mmol, Example 155d) and iodomethane (0.063 mL, 1.0 mmol, Aldrich) in DMF (3.0 mL) with stirring at room temperature. The mixture was stirred for 30 min at room temperature, diluted with EtOAc (30 mL), washed with water (20 mL) and brine (20 mL), dried over Na2SO4, and filtered. The filtrate was evaporated in vacuo and the residue was purified by silica gel column chromatography, eluting with 80% EtOAc/hexane to give the title compound. MS (ESI, pos. ion) m/z: 233 (M+1).
Loading…
