Dimethylformamide → HCID 22638733, compound

Participants

Reaction Steps

Phosphorous oxychloride (0.23 g, 1.47 mmol) was added to dimethylformamide (2 mL) at room temperature with stirring. After 15 min, [2-(1H-indol-6-yl)-cyclopropylmethyl]-dimethyl-amine (0.35 g, 1.64 mmol) in DMF (3 mL) was added dropwise. After 20 h, the reaction was quenched with ice and 1 N NaOH. The solution was extracted with methylene chloride, dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to give 6-(2-dimethylaminomethyl-cyclopropyl)-1H-indole-3-carbaldehyde of an oil (0.25 g, 63%) that was used for the next reaction without purification. 1H NMR (CDCl3): δ 9.84 (s, 1H), 8.14 (d, J=8.4 Hz, 1H), 7.97 (s, 1H), 7.14 (d, J=8.4 Hz, 1H), 7.05 (s, 1H), 2.64 (s, 1H), 2.56 (s, 7H), 1.91 (m, 1H), 1.27 (m, 1H), 1.06 (m, 1H), and 0.92 (m, 1H).

Provenance & Evidence