Ammonium Chloride → 4-[(5-Chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)-N-(methylsulfonyl)benzamide

Participants

Reaction Steps

To a solution of 4-[(5-chloro-6-isopropoxypyridin-3-yl)oxy]-3-(2-methoxypyridin-3-yl)benzamide (Preparation 27, 436 mg, 1.05 mmol) in anhydrous THF (10.0 mL) was added lithium bis(trimethylsilyl) amide (1.0 M in THF, 2.63 mL, 2.63 mmol). The solution was stirred for 30 minutes before the addition of methanesulfonyl chloride (210 uL, 2.63 mmol). The reaction mixture was stirred for 1 hour and then a saturated aqueous solution of ammonium chloride (25 mL) was added to the reaction mixture. The reaction mixture was partitioned between water (30 mL) and EtOAc (25 mL). The aqueous phase was separated and extracted with EtOAc (2×25 mL). The combined organic extracts were dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to afford a solid. The material was purified by silica gel column chromatography, eluting with 60:40:1 heptane/EtOAc/acetic acid. Fractions containing product were combined and concentrated in vacuo to obtain the title compound as a solid (230 mg):

Provenance & Evidence