Potassium Phosphate, Tribasic → [6-Fluoro-3-methyl-4-(4-methyl-benzyl)-naphthalen-2-yl]-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

A mixture of (6-fluoro-3-methyl-4-trifluoromethanesulfonyloxy-naphthalen-2-yl)-acetic acid methyl ester (220 mg, 0.578 mmol), 4,4,5,5-tetramethyl-2-(4-methyl-benzyl)-1,3,2-dioxaborolane (402 mg, 1.731 mmol), palladium(II) acetate (17 mg, 0.0757 mmol), 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl (53 mg, 0.129 mmol), potassium phosphate (246 mg, 1.159 mmol), toluene (5 mL) and water (0.5 mL) was heated at 110° C. for 2 hours. The reaction mixture was cooled to room temperature, diluted with ethyl acetate (100 mL) and washed with brine (25 mL). The organic phase was dried over MgSO4, filtered and concentrated. Silica gel chromatography (93:7 hexanes-ethyl acetate) gave 145.7 mg (74.9%) of [6-fluoro-3-methyl-4-(4-methyl-benzyl)-naphthalen-2-yl]-acetic acid methyl ester as a colorless oil which solidified on standing. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.92 (dd, J=8.8, 6.2 Hz, 1 H), 7.75 (s, 1 H), 7.63 (dd, J=12.4, 2.1 Hz, 1 H), 7.33 (td, J=8.8, 2.1 Hz, 1 H), 7.03 (d, J=7.8 Hz, 2 H), 6.92 (d, J=7.8 Hz, 2 H), 4.40 (s, 2 H), 3.93 (s, 2 H), 3.64 (s, 3 H), 2.30 (s, 3 H), 2.21 (s, 3 H).

Provenance & Evidence