Hydrochloric Acid → HCID 58094953, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of ethyl 5-(2-methylpyrazolo[1,5-a]pyridin-3-yl)-3-phenylthiophene-2-carboxylate (119 mg, 0.327 mmol), a 8N aqueous solution of sodium hydroxide (5 mL), THF (5 mL) and ethanol (10 mL) and water (1 mL) was stirred for 1 h at 70° C. The mixture was allowed to cool to 0° C. To the mixture, was added a 6N aqueous solution of hydrogen chloride to adjust ca pH 3-4. The mixture was extracted with EtOAc-THF mixed solvent and the organic phase was washed with brine and dried over anhydrous magnesium sulfate. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was washed with diisopropyl ether and dried under vacuum to yield the title compound (112 mg, over yield) as a pale yellow solid. 1H NMR (300 MHz, d6-DMSO) δ: 12.83 (br s, 1H), 8.80-8.65 (m, 1H), 8.00-7.93 (m, 1H), 7.61-7.53 (m, 2H), 7.44-7.36 (m, 4H), 7.28 (s, 1H), 7.02-6.95 (m, 1H), 2.60 (s, 3H).

Provenance & Evidence