Sodium Carbonate → {6-Fluoro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester

A stirred solution of (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (0.20 g, 0.52 mmol) in dimethoxyethane (10 mL) was purged with argon for 5 minutes at room temperature. Triphenylphosphine (0.031 g, 0.12 mmol), palladium (II) acetate (0.013 g, 0.06 mmol), 1-(4-boronophenylsulfonyl)piperidine (0.191 g, 0.71 mmol) and a 2 M aqueous solution of sodium carbonate (1.0 mL, 2.0 mmol) were added simultaneously to the reaction mixture at room temperature under argon. The reaction mixture was refluxed for 2 hours and then cooled to room temperature. Water was added and the mixture was extracted twice with ethyl acetate. The collected organic extracts were washed with water and then brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to give the crude product, which was finally purified using flash chromatography (Biotage, 5-10% ethyl acetate-hexane) to {6-fluoro-3-methyl-4-[4-(piperidine-1-sulfonyl)-phenyl]-naphthalen-2-yl}-acetic acid methyl ester (0.195 g, 84%) as a solid. MS calcd. for C25H25FNO4S [(M−H)−] 454, obsd. 454.2 (low intensity).

1. temperatureThe reaction mixture was refluxed for 2 hours
2. extractionthe mixture was extracted twice with ethyl acetate
3. washThe collected organic extracts were washed with water
4. dry with materialbrine, dried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure

ORD record

ord-90833010a24941f39e1c375fbd4dcc76

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000044B2