Sodium Carbonate → 2'-({5-[3,5-Bis(trifluoromethyl)phenyl]-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-methoxy-4'-(trifluoromethyl)biphenyl-3-carbaldehyde

Participants

Reaction Steps

A mixture of 5-[3,5-bis(trifluoromethyl)phenyl]-3-[2-iodo-5-(trifluoromethyl)benzyl]-1,3-oxazolidin-2-one (Example 66, 50 mg; 0.0858 mmol), 5-formyl-2-methoxyphenyl boronic acid (46 mg; 0.257 mmol), tetrakis(triphenylphosphine)palladium (0) (12 mg; 0.0103 mmol), and sodium carbonate (74 mg) in benzene/ethanol/water (2.8/0.4/1.2 mL) was heated at reflux for 60 h. The reaction was diluted with EtOAc (30 mL) and washed successively with H2O (10 mL) and brine (10 mL), dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified by flash silica gel chromatography (0-50% EtOAc/hexanes gradient) to afford 2′-({5-[3,5-bis(trifluoromethyl)phenyl]-2-oxo-1,3-oxazolidin-3-yl}methyl)-6-methoxy-4′-(trifluoromethyl)biphenyl-3-carbaldehyde as a yellow oil. LCMS=592.1 (M+1)+. 1H NMR (CDCl3, 500 MHz, mixture of atropisomers): δ 9.98 (s, 1H), 7.99-7.96 (m, 1H), 7.90 (s, 1H), 7.75 (s, 2H), 7.69-7.64 (m, 2 Hz), 7.53 (s, 1H), 7.41-7.38 (m, 1H), 7.17-7.14 (m, 1H), 5.37 (t, J=8.2 Hz, 1H), 4.59 (d, J=15.3 Hz, 1H), 4.37 (d, J=15.6 Hz, 1H), 3.92 (s, 3H), 3.67-3.64 (m, 1 Hz), 3.19-3.16 (m, 1H).

Provenance & Evidence