(Diethylamino)sulfur trifluoride → methyl 6-(2-fluorocyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate

Participants

Reaction Steps

Diethylaminosulfur trifluoride (1.2 eq.) was added at −60° C. to a 0.1M solution of methyl 6-(2-hydroxycyclohexyl)-4H-thieno[3,2-b]pyrrole-2-carboxylate in dry EtOAc, and the mixture was stirred at this temperature for 1 h, then allowed to warm slowly to RT. Aq. NaHCO3-solution was added and the mixture was extracted with EtOAc; the organic layer was washed with water and brine, dried on Na2SO4 and concentrated. Chromatography (PE/EtOAc) afforded the title compound (73%). 1H-NMR (300 MHz, CDCl3, 300 K, δ) 8.31 (bs, 1H), 7.67 (s, 1H), 7.06 (s, 1H), 4.53 (dtd, 1H, J 48.6, 10.1, 4.5), 3.88 (s, 3H), 2.88-2.77 (m, 1H), 2.41-1.17 (m, 8H); MS (ES+) m/z 282 (M+H)+.

Provenance & Evidence