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

A stirred solution of (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (0.10 g, 0.26 mmol) in dimethoxyethane (5 mL) for 5 minutes at room temperature. Triphenylphosphine (0.016 g, 0.006 mmol), palladium (II) acetate (0.007 g, 0.003 mmol), 4-(N-(4-methoxybenzyl)sulfamoyl)phenylboronic acid (0.135 g, 0.35 mmol) and a 2 M aqueous solution of sodium carbonate (0.5 mL, 1.0 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 afford {6-fluoro-4-[4-(4-methoxy-benzylsulfamoyl)-phenyl]-3-methyl-naphthalen-2-yl}-acetic acid methyl ester (0.055 g, 41%) as a solid. MS calcd. for C28H25FNO5S [(M−H)−] 506, obsd. 506.2.

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
6. customto give the crude product, which
7. customwas finally purified

ORD-Eintrag

ord-96b5b1a85b8e453880fe1d3d2df38e38

Quelldatensatz

uspto-grants-2015_04

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US09000044B2