Trifluoroacetic acid → HCID 69097147, compound

Participants

Reaction Steps

To a solution of triethylsilane (0.202 mL) and trifluoroacetic acid (0.049 mL) in dichloromethane (2 mL) was added a suspension of 2-tert-butyl-5-chloro-6-methoxy-1H-indole (100 mg) and methyl 6-formylpyridine-2-carboxylate (76.2 mg) in dichloromethane (1.5 mL) under ice-cooling, and this mixture was stirred at room temperature overnight. To the reaction mixture was added water, and then the resulting mixture was alkalified by the addition of sodium hydrogen carbonate. The organic layer was separated and concentrated under reduced pressure. The residue was purified by aminopropylated silica gel column chromatography (eluting solvent: ethyl acetate-hexane) to obtain the title compound (152 mg). 1H-NMR (CDCl3) δ ppm: 1.39 (9H, s), 3.90 (3H, s), 4.05 (3H, s), 4.52 (2H, s), 6.91 (1H, s), 6.95-7.05 (1H, m), 7.28 (1H, s), 7.60 (1H, t, J=7.8 Hz), 7.80-8.20 (2H, m).

Provenance & Evidence