Dimethylformamide → HCID 66609499, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 1,1′-bis(diphenylphosphino)ferrocene (25 mg, 0.045 mmol), zinc cyanide (55 mg, 0.47 mmol), and 7-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline from Example 7 Step E (150 mg, 0.376) was added tris(dibenzylideneacetone)dipalladium (34 mg, 0.031 mmol) in DMF (3 mL). The reaction vessel was evacuated, and flushed with argon (2×), then the mixture was heated at 90° C. overnight during which time most of the solvent evaporated. The mixture was diluted with EtOAc (20 mL) and washed with water (20 mL), 2N NH4OH (20 mL), and brine, dried over Na2SO4, and concentrated under reduced pressure onto Celite. The mixture was purified by silica gel chromatography eluting with a 10-60% EtOAc/hexanes to afford 2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline-7-carbonitrile as a solid (0.103 g, 79%). LC-MS (ESI) m/z 347 (M+H)+

Provenance & Evidence