Water → HCID 57494746, compound

Participants

Reaction Steps

A solution of N,N-Dimethylformamide (150 mL) and 2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridine (10.3 g, 33 mmol) was cooled to 0° C. and treated with phosphorous oxychloride (4.7 mL, 50 mmol). After the addition was complete, the mixture was warmed to room temperature and the resultant solution was stirred over the weekend. Water was added, followed by dichloromethane. The aqueous layer was extracted with dichloromethane. The combined organics were washed with brine, dried over magnesium sulfate, filtered and concentrated. The residue was washed with diethyl ether and hexanes to give 2-(3-bromophenyl)-7-chloropyrazolo[1,5-a]pyridine-3-carbaldehyde (10.6 g, 96%) as a fluffy white solid. 1H NMR (DMSO-d6): δ 10.09 (s, 1 H), 8.37 (d, 1 H), 8.11 (d, 1H), 7.95 (d, 1H), 7.80 (m, 2 H), 7.65 (d, 1 H), 7.55 (m, 1 H).

Provenance & Evidence