Cesium carbonate → HCID 66610440, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 8-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline from Example 35 step B (250 mg, 0.625 mmol), tris(dibenzylideneacetone)dipalladium (57 mg, 0.063 mmol), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (108 mg, 0.187 mmol), methanesulfonamide (83 mg, 0.87 mmol) and Cs2CO3 (284 mg, 0.87 mmol) was added dioxane (5 mL). The reaction vessel was evacuated and flushed with argon (3×), and the mixture was heated at 100° C. overnight. The mixture was allowed to cool and was then diluted with DCM and concentrated under reduced pressure onto Celite. The residue was purified by silica gel flash chromatography eluting with 10-100% EtOAc/hexanes to afford impure N-(2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazolin-8-yl)methanesulfonamide (220 mg, 85%). LC-MS (ESI) m/z 415 (M+H)+.

Provenance & Evidence