Sodium methanethiolate → 2-(Trifluoromethyl)imidazo[1,2-a]pyridine-6-thiol

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Reaction Conditions

Reaction Steps

A mixture of 6-bromo-2-(trifluoromethyl)imidazo[1,2-a]pyridine (500 mg, 1.89 mmol) (for the synthesis, see WO2005111047) and sodium thiomethoxide (400 mg, 5.67 mmol) in dimethylacetamide (5 ml) was heated to 150° C. for 90 minutes under a nitrogen atmosphere. The resultant mixture was cooled down to room temperature and partitioned between ethyl acetate and an aqueous solution of ammonium chloride. The aqueous phase was extracted with more ethyl acetate and the combined organic layers were washed with water and brine, dried over magnesium sulfate and concentrated in vacuo to afford the title compound as a red oil (251 mg, 61% yield). MS (ES+) 219, (ES+) 217.

Provenance & Evidence