Sodium Carbonate → HCID 86695024, compound

A stirred solution of (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (0.200 g, 0.52 mmol) in dimethoxyethane (10 mL) for 5 minutes at room temperature. Triphenylphosphine (0.031 g, 0.12 mmol), palladium (II) acetate (0.013 g, 0.060 mmol), 4-(N-isopropyl-N-(4-methoxybenzyl)sulfamoyl)phenyl-boronic acid (0.258 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 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 afford (6-fluoro-4-{4-[isopropyl-(4-methoxy-benzyl)-sulfamoyl]-phenyl}-3-methyl-naphthalen-2-yl)-acetic acid methyl ester (0.17 g, 61%) as a solid. MS calcd. for C31H31FNO5S [(M−H)−] 548, obsd. 548.4.

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 and brine
4. dry with materialdried over anhydrous Na2SO4
5. concentrationconcentrated under reduced pressure
6. customto give the crude product, which
7. customwas finally purified

ORD record

ord-6ead6ac70c2f460d8501761aa1271d22

Source dataset

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09000044B2