Aluminum(III) Chloride → methyl 5-chloro-3-methyl-1H-indole-7-carboxylate

Participants

Reaction Conditions

Reaction Steps

Methyl 5-chloro-3-methyl-2-(trimethylsilyl)-1H-indole-7-carboxylate (510 mg, 1.73 mmol) from Step A above and aluminum chloride (254 mg, 1.9 mmol) were added to methylene chloride (5 mL) and the reaction mixture was stirred for 3 h at 0° C. The reaction was quenched with water, extracted with ether, dried over sodium sulfate, filtered, and concentrated to afford methyl 5-chloro-3-methyl-1H-indole-7-carboxylate (410 mg, quantitative yield) as a dark green solid: 1H NMR (500 MHz, CDCl3) δ 8.09 (s, 1H), 8.01 (d, J=1.0 Hz, 1H), 7.87 (d, J=1.0 Hz, 1H), 4.01 (s, 3H), 3.40 (s, 3H); MS (ESI+) m/z 224 (M+H).

Provenance & Evidence