Trifluoroacetic acid → ethyl 2-(2-(acetylthio)-1H-indol-3-yl)acetate

Participants

Reaction Steps

A solution of tert-butyl 2-bromo-3-(2-ethoxy-2-oxoethyl)-1H-indole-1-carboxylate (500 mg, 1.3 mmol), potassium ethanethioate (200 mg, 1.7 mmol), tris(dibenzylideneacetone)dipalladium(0) (60 mg, 0.065 mmol), xantphos (75 mg, 0.13 mmol) and DIPEA (0.5 ml, 2.6 mmol) in 1,4-dioxane (4 ml), was heated at 150° C. for 20 minutes in a microwave reactor. TFA (5 ml) was added to the mixture and stirred for 1 hour until Boc deprotection was complete. Filtered reaction mixture through celite and washed with EtOAc (2×50 ml). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product was introduced to a silica gel loading column and purified by column chromatography (10-30% EtOAc/Hexanes) to provide the desired product (190 mg, 0.69 mmol), 52.8%. MS (m/z) 278 [M+H]+.

Provenance & Evidence