Methanol → Methyl 6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate

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Reaction Conditions

Reaction Steps

Thionyl chloride (2.0 mL) was added dropwise to a solution of 6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylic acid (4.0 g, 18.5 mmol) in MeOH (100 mL) under cooling in an ice bath. The resulting mixture was stirred at 80° C. for more than 16 h. The reaction mixture was then cooled to room temperature and concentrated, and the crude product was purified by flash chromatography (silica gel, 1% to 10% MeOH in CH2Cl2) to give the methyl 6-chloro-3-methyl-[1,2,4]triazolo[4,3-b]pyridazine-8-carboxylate as a yellow solid (3.0 g, 72% yield). 1H NMR (300 MHz, CD3OD): δ 7.92 (s, 1H), 4.07 (s, 3H), 2.79 (s, 3H). LRMS [M+H]+: 226 m/z.

Provenance & Evidence