Thiophenol → tert-butyl 6-chloro-8-(phenylthio)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 8-bromo-6-chloro-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (1.00 g, 2.58 mmol), benzenethiol (0.40 mL, 3.87 mmol), di-palladium-tris(dibenzylideneacetone) (118 mg, 0.13 mmol), N,N-diisopropylethylamine (0.9 mL, 5.16 mmol) and xantphos (149 mg, 0.26 mmol) were suspended in anhydrous dioxane (10 mL). The reaction flask was purged with argon and the mixture heated to 110° C. for 14 h. After cooling, the reaction mixture was diluted with dichloromethane and filtered through a celite bed. The filtrate was concentrated in vacuo and the residue purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give tert-butyl 6-chloro-8-(phenylthio)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (1.10 g, 91%) as an off-white solid: 1H NMR (CDCl3, 400 MHz) δ 7.47-7.38 (m, 1H), 7.34 (d, J=1.2 Hz, 1H), 7.31-7.27 (m, 1H), 7.26-7.25 (m, 2H), 7.24-7.19 (m, 2H), 4.50 (s, 2H), 3.86-3.79 (m, 2H), 2.92-2.87 (m, 2H), 1.50 (s, 9H).

Provenance & Evidence