tert-Butyl acrylate → HCID 89602354, compound

Participants

Reaction Conditions

Reaction Steps

A solution of 58b (640 mg, 2.14 mmol), tert-butyl acrylate (1.37 g, 10.7 mmol), DIPEA (0.74 ml, 4.28 mmol), Pd-(OAc)2 (47 mg, 0.21 mmol) and P (o-tol)3 (129 mg, 0.42 mmol) in propionitrile (8 ml) and DMF (2 ml) was purged with nitrogen for 10 minutes, and then was heated at 100-110° C. for 16 h. The progress of the reaction was monitored by TLC. After 16 h of stirring, the reaction mixture was cooled to 20-35° C., filtered through celite, and then concentrated. The resultant residue was diluted with water (50 ml) and extracted with ethyl acetate (2×50 ml). The combine organic layers were washed with brine (50 ml), followed by drying over anhydrous Na2SO4 and filtering. The filtrate was rotary evaporated to get residue which was purified by column chromatography using a mixture of 60% ethyl acetate/pet ether as an eluent to get the desired compound as an off-white solid (560 mg, 75%). 1H NMR (400 MHz, DMSO-d6) δ 10.17 (s, 1H), 8.60 (d, J=2.0 Hz, 1H), 8.20 (dd, J=8.8, 2.5 Hz, 1H), 8.11 (d, J=8.8 Hz, 1H), 7.53 (d, J=16.1 Hz, 1H), 6.56 (d, J=16.2 Hz, 1H), 3.62 (t, J=4.4 Hz, 4H), 3.21 (s, 2H), 2.55-2.51 (m, 4H), 1.48 (s, 9H); MS (ES) m/e 348.0 (M+H)+.

Provenance & Evidence