Diisopropylamine → 2-(2-Chlorophenylamino)-3,4-difluoro-5-trimethylsilanylethynylbenzoic acid methyl ester

Participants

Reaction Steps

A mixture of 5-bromo-2-(2-chlorophenylamino)-3,4-difluorobenzoic acid methyl ester (8.02 g, 21.3 mmol, prepared as described in Example 1), TMS-acetylene (3.80 mL, 26.4 mmol), Pd(PPh3)2Cl2 (1.52 g, 2.12 mmol), CuI (405 mg, 2.12 mmol), and i-Pr2NH (6.00 mL, 42.6 mmol) in THF (120 mL) was stirred for 3 days 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, and filtered. The organic layer was concentrated to give the crude material which was purified by silica gel flash column chromatography (100% Hexane to 1% to 2% EtOAc in Hexane) to afford the desired product (7.11 g, 85%).

Provenance & Evidence