Sodium Carbonate → HCID 66898238, compound

Participants

Reaction Conditions

Reaction Steps

Tetrabutylammonium chloride (100 mg, 0.4 mmol), trimethyl(prop-1-ynyl)silane (1.1 ml, 7.2 mmol), methyl 2-amino-5-chloro-3-iodobenzoate (1.0 g, 3.6 mmol), triphenylphosphine (47.2 mg, 0.1 mmol), palladium(II) acetate (20 mg, 0.1 mmol) and sodium carbonate (1.9 g, 18 mmol) in DMF were added to a sealed tube and the reaction was stirred at 100° C. for 15 h. After cooling to room temperature, the reaction mixture was diluted with ether and washed with saturated aqueous ammonium chloride and water. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude material was then purified by column chromatography (silica gel, 70:30 hexanes/ethyl acetate) to afford methyl 5-chloro-3-methyl-2-(trimethylsilyl)-1H-indole-7-carboxylate (620 mg, 59%) as a light yellow solid: 1H NMR (500 MHz, CDCl3) δ 9.50 (s, 1H), 7.80 (d, J=1.0 Hz, 1H), 7.72 (d, J=1.0 Hz, 1H), 3.98 (s, 3H), 2.37 (s, 3H), 0.40 (t, 9H); MS (ESI+) m/z 296 (M+H).

Provenance & Evidence