Triethylamine → HCID 57444730, compound

Participants

Reaction Steps

To a solution of 1-(3-bromo-4-methoxyphenyl)-2-(6-chloro-2-pyridinyl)ethanone oxime (1.00 g, 2.8 mmol) in dimethoxyethane (30 mL) at 0° C. was added slowly methylsulfonyl chloride (0.24 mL, 3.08 mmol). The reaction was stirred for 15 minutes and then triethylamine (1.7 mL, 12.3 mmol) in dimethoxyethane (3 mL) was added to the reaction. Upon addition of the triethylamine a precipitate formed. Once the addition of the triethylamine solution had been completed the reaction mixture was allowed to warm to room temperature and was stirred for 1 hour. The precipitate was removed by filteration and the precipitate was washed with dimethoxyethane. To the combined filtrate was added iron (II) chloride (14 mg, 0.12 mmol) and the resulting mixture was heated at 80° C. for 15 hours. The reaction mixture was allowed to cool to room temperature. Ethyl acetate was added to dilute the mixture and the organic phase was washed with water, brine and dried (magnesium sulfate). Filtration and concentration of the filtrate, followed by flash chromatography (4:6 ethyl acetate:hexanes) gave 2-(3-bromo-4-methoxyphenyl)-7-chloropyrazolo[1,5-a]pyridine (86 mg, 9%). 1H NMR (CDCl3): δ 8.21 (d, 1H), 7.95 (d, 1H), 7.48 (d, 1H), 7.10 (t, 1H), 6.98 (d, 1H), 6.88 (d, 1H), 6.84 (s, 1H), 3.96 (s, 3H); MS m/z 337 (M+1).

Provenance & Evidence