Potassium Carbonate → HCID 56602322, compound

Participants

Reaction Steps

To a solution of ethyl 2-(5-bromo-3-methyl-1-(trifluoromethylsulfonyloxy)naphthalen-2-yl)-2-oxoacetate (1.2 g, 2.56 mmol) and 4-chlorophenylboronic acid (440 mg, 2.81 mmol) in toluene was added 2 M potassium carbonate (2.8 mL, 5.63 mmol) and PdCl2(dppf) (187 mg, 0.256 mmol) and the reaction was degassed with argon 10 minutes. The reaction was stirred at room temperature for 4 hours. The reaction was filtered, diluted with water, extracted with ethyl acetate and concentrated. The crude reaction was purified by flash column chromatography (silica gel, ethyl acetate/hexanes) followed by reverse phase HPLC (Gemini, 40-100% ACN/H2O+0.1% TFA). Product was lyophilized to give 670 mg of ethyl 2-(5-bromo-1-(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate (36A) as a yellow oil, 1H-NMR: 400 MHz, (CDCl3) δ: 8.20 (s, 1H), 8.13 (d, J=8.8 Hz, 1H), 7.85 (d, J=6.8 Hz, 1H), 7.68 (t, J=7.2 Hz, 1H), 7.51 (d, J=8.8 Hz, 2H), 7.39 (d, J=8.4 Hz, 2H), 3.95 (q, J=6.8 Hz, 2H), 2.41 (s, 3H), 1.14 (t, J=7.2 Hz, 5H); and 109 mg of ethyl 2-(1,5-bis(4-chlorophenyl)-3-methylnaphthalen-2-yl)-2-oxoacetate (36B) as a white solid. 1H-NMR: 400 MHz, (CDCl3) δ: 7.72 (s, 1H), 7.59-7.56 (m, 1H), 7.50 (t, J=8.0 Hz, 2H), 7.46-7.44 (m, 5H), 7.43 (d, J=2.4 Hz, 1H), 7.28 (d, J=8.0 Hz, 2H), 3.94 (q, J=7.2 Hz, 2H), 2.42 (s, 3H), 1.14 (t, J=7.2 Hz, 3H).

Provenance & Evidence