Sodium hydride → methyl 6-(2-fluorocyclohexyl)-4-(2-methoxy-2-oxoethyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

60% NaH in mineral oil (2 eq.) was added at RT to a 0.25M solution of methyl 6-(2-fluorocyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in dry DMF, after few min methyl bromoacetate (3 eq.) was added and the mixture was stirred at 60° C. for 1 h and left overnight at RT. After dilution with EtOAc, the organic layer was washed with 1N HCl, sat. NaHCO3 and brine, dried over Na2SO4 and concentrated. Chromatography (PE/EtOAc) afforded the title compound (53%). 1H-NMR (400 MHz, CDCl3, 300K, δ) 7.60 (s, 1H), 6.92 (s, 1H), 4.74 (s, 2H), 4.50 (dtd, 1H, J 48.9, 10.3, 4.5), 3.88 (s, 3H), 3.77 (s, 3H), 2.85-2.76 (m, 1H), 2.25-2.11 (m, 2H), 1.90-1.74 (m, 2H), 1.68-1.54 (m, 2H), 1.44-1.33 (m, 2H); MS (ES+) m/z 354 (M+H)+.

Provenance & Evidence