Dimethylformamide → HCID 86695025, compound

Participants

Reaction Steps

To a mixture of 4-(methanesulfonyl)benzeneboronic acid (146 mg, 0.734 mmol), (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (93 mg, 0.244 mmol), 1,1′-bis(diphenylphosphino)ferrocenedichloropalladium (II) (36 mg, 0.048 mmol), and cesium carbonate (239 mg, 0.734 mmol) was added anhydrous DMF (5 mL) at room temperature. The resulting light brown suspension was heated to reflux for 15 hours. The reaction mixture was cooled to room temperature and diluted with brine and ethyl acetate. The two layers were separated and the aqueous layer was extracted with ethyl acetate and the combined extracts were washed with brine. The organic layer was dried over anhydrous MgSO4, filtered, and concentrated to give the crude residue. Flash chromatography (80 g ISCO column, 0-45% ethyl acetate in hexanes) gave 80 mg (85%) of [6-fluoro-4-(4-methansulfonyl-phenyl)-3-methyl-naphthalen-2-yl]-acetic acid methyl ester. 1H NMR (300 MHz, CDCl3) δ ppm 8.11 (d, J=8.2 Hz, 2 H), 7.82 (dd, J=8.7, 5.9 Hz, 1 H), 7.77 (s, 1 H), 7.49 (d, J=8.2 Hz, 2 H), 7.21 (td, J=8.7, 2.3 Hz, 1 H), 6.77 (dd, J=11.2, 2.3 Hz, 1 H), 3.87 (s, 2 H), 3.74 (s, 3 H), 3.20 (s, 3 H), 2.13 (s, 3 H). HRMS cald. for C21H20FO4S [(M+H)+] 387.1061, obsd. 387.1059.

Provenance & Evidence