Diisopropylethylamine → {6-Fluoro-4-[1-(pyridine-3-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester

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Reaction Steps

Diisopropylethylamine (0.3 mL, 1.7 mmol) was added at 0° C. to a solution of (6-fluoro-4-piperidin-4-yl-naphthalen-2-yl)-acetic acid methyl ester trifluoroacetate salt (which may be prepared as described above; 150 mg, 0.36 mmol) in CH2Cl2 (6 mL). The solution was stirred at room temperature for 30 minutes and then a solution of pyridine-3-sulfonyl chloride (which may be prepared as described above; 320 mg, 1.8 mmol) in CH2Cl2 (1 mL) was added. The mixture was stirred at room temperature for 16 hours. The solvent was evaporated under reduced pressure. The residue was purified by chromatography on silica gel using a Biotage purification system, eluting with 30% ethyl acetate/hexanes, to give {6-fluoro-4-[1-(pyridine-3-sulfonyl)-piperidin-4-yl]-naphthalen-2-yl}-acetic acid methyl ester (85 mg, 53%) as a sticky white solid. MS cald. for C23H24FN2O4S [(M+H)+]: 443, obsd. 443.2.

Provenance & Evidence