反应详情

A mixture of 6-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (2.61 g, 6.93 mmol), TMS-acetylene (1.18 mL, 8.32 mmol), Pd(PPh3)2Cl2 (496 mg, 0.693 mmol), CuI (132 mg, 0.693 mmol), and i-Pr2NH (1.95 mL, 13.9 mmol) in THF (11 mL) was stirred for 16 hours at room temperature. The reaction mixture was concentrated in vacuo, diluted with EtOAc, and washed with saturated aqueous NH4Cl and brine. The organic layer was dried over MgSO4, filtered, and concentrated to give the crude material that was purified by silica gel flash column chromatography (100% hexanes to 1% to 2% EtOAc in hexanes) to afford the desired product (2.15 g, 79%).

1. concentrationThe reaction mixture was concentrated in vacuo
2. additiondiluted with EtOAc
3. washwashed with saturated aqueous NH4Cl and brine
4. dry with materialThe organic layer was dried over MgSO4
5. filtrationfiltered
6. concentrationconcentrated
7. customto give the crude material that
8. customwas purified by silica gel flash column chromatography (100% hexanes to 1% to 2% EtOAc in hexanes)