Tributylvinyltin → Benzyl 6-[(tert-butoxycarbonyl)amino]-2-methyl-3-vinylbenzoate

Participants

Reaction Conditions

Reaction Steps

A mixture of Example 126A (1.4 g, 3.3 mmol), DMF (33 mL) and tributyl(vinyl)tin (1.1 mL, 3.8 mmol) was degassed with argon 30 minutes, treated with Pd(PPh3)4 (577 mg, 0.5 mmol), heated to 90° C. for 18 hours, and concentrated. The concentrate was purified by flash column chromatography on silica gel (200 g) with 50% dichloromethane/hexanes to provide the desired product. MS (ESI(+)) m/e 368 (M+H)+; (ESI(−)) m/e 366 (M−H)−; 1H NMR (300 MHz, DMSO-d6) δ 8.87 (s, 1H), 7.54 (d, 1H), 7.45 (m, 2H), 7.37 (m, 3H), 7.27 (d, 1H), 6.94 (dd, 1H), 5.64 (dd, 1H), 5.31 (dd, 1H), 5.27 (s, 2H), 2.21 (s, 3H), 1.42 (s, 9H).

Provenance & Evidence