Water → 4-(5-chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)benzamide

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Reaction Steps

To a solution of 4-(5-chloro-6-cyclopropylpyridin-3-yloxy)-3-(2-methoxypyridin-3-yl)benzamide (Preparation 40, 437 mg, 1.10 mmol) in anhydrous tetrahydrofuran (4 mL) under nitrogen was added 1M solution of lithium bis(trimethylsilyl)amide in tetrahydrofuran (4.40 mL, 4.40 mmol). The solution was stirred 30 minutes at room temperature then methane sulfonyl chloride (340 μL, 4.40 mmol) was added and the reaction mixture was stirred 2 hours at room temperature. Water (50 mL) was added and the solution was extracted with ethyl acetate (3×20 mL). The organic layers were combined, dried over magnesium sulfate, filtered and concentrated in vacuo. The crude material was purified by silica gel column chromatography eluting with Feb. 10, 1990 acetic acid/ethyl acetate/dichloromethane to afford the title compound as a white solid (230 mg, 44%).

Provenance & Evidence