Methanol → HCID 16762498, compound

Participants

Reaction Steps

A 2.0 M solution of oxalyl chloride in methylene chloride (4.50 mL, 9.0 mmol) was added to a solution of 5-fluoroindole (1.14 g, 8.4 mmol) in ether (19 mL) dropwise over 10 min at 4° C. under N2. The ice bath was removed and the resulting mixture was stirred for 2 h. A 25% sodium methoxide in methanol solution (4.3 mL, 18.8 mmol) was added at −78° C. over 5 min. The mixture was allowed to warm up to room temperature and stirred for 1 h. The reaction was quenched with water (50 mL), filtered and rinsed with cold ether to afford the title compound (1.34, 72%) as a yellow solid. 1H NMR (DMSO-d6) δ 12.51 (bs, 1H), 8.56 (s, 1H), 7.86 (m, 1H), 7.60 (m, 1H), 7.15 (m, 1H), 3.90 (s, 3H).

Provenance & Evidence