ethyl 6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate → HCID 69516741, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1.00 g (2.31 mmole) of ethyl-6-chloro-8-iodo-2-(trifluoromethyl)-2H-chromene-3-carboxylate, 134 mg (0.116 mmole) tetrakis(triphenylphosphine)palladium(O), 44 mg (0.231 mmole) copper (I) iodide, 20 mL degassed toluene and 0.965 mL (6.94 mmole) degassed TEA was cooled to −78° C. and treated with an excess of condensed gaseous 1-butyne. The mixture was stirred for thirty minutes at −78° C. and allowed to warm to room temperature and stirred overnight. The reaction mixture was concd and the resulting oil was purified using reverse phase chromatography to afford 0.768 g (93%) of a crystalline solid: 1H NMR (CDCl3/400 MHz) 1.24 (t, 3H, J=7.2 Hz), 1.34 (t, 3H, J=7.2 Hz), 2.45 (q, 2H, J=7.6 Hz), 4.27-4.35 (m, 2H), 5.78 (q, 1H, J=6.8 Hz), 7.10 (d, 1H, J=2.4 Hz), 7.32 (d, 1H, J=2.4 Hz), 7.59 (s, 1H); MS (ES+) 359 (M+1, 100).

Provenance & Evidence