Water → HCID 59508110, compound

Participants

Reaction Conditions

Reaction Steps

To a suspension of methyl 2-(2-methoxypyridin-3-yl)-1H-indole-5-carboxylate (1.0 g, 0.354 mmol) in methanol (100 ml) was added lithium hydroxide (0.30 g, 1.25 mmol) and water (10 ml). The reaction was heated overnight at 80° C. The reaction was not complete so more lithium hydroxide (0.10 g, 0.42 mmol) was added and heating was continued for 4 hours. The reaction was allowed to cool and stir at room temperature overnight. The reaction was concentrated to about 15 ml and 1 g citric acid dissolved in 10 ml of water was added. The solid was filtered, washed with water (25 ml) and dried under high vacuum at 50° C. The desired product was obtained as a white solid and used in the next reaction without any purification (0.9 g, 94%). 400 MHz 1H NMR (DMSO-d6) δ: 12.56 (bs, 1H), 11.69 (s, 1H), 8.30-8.12 (m, 3H), 7.75 (dd, J=1.6 Hz, 8.5 Hz, 1H), 7.50 (d, J=8.8 Hz, 1H), 7.24-7.09 (m, 2H), 4.06 (s, 3H). LCMS: 269 [M+H]

Provenance & Evidence