Sodium Carbonate → HCID 136337209, compound

Participants

Reaction Conditions

Reaction Steps

A vial was charged with 2,4-dichloropyrimidine (362 mg, 2.43 mmol), 2-hydroxy-3-trifluoromethylphenylboronic acid (250 mg, 1.21 mmol) and trans-dichlorobis(triphenylphosphine)palladium (II) (42.6 mg, 0.061 mmol). Acetonitrile (6 mL) and sodium carbonate (3.0 mL, 1.0 M aqueous, 3.0 mmol) were added, and the resulting mixture was degassed via nitrogen sparge. The reaction mixture was stirred at 70° C. for 6 h, then was allowed to cool to ambient temperature and was poured into water. The mixture was extracted with EtOAc, and the organic phase was concentrated in vacuo. Purification by chromatography on silica gel (0 to 25% EtOAc in hexanes, then 25 to 100% EtOAc in hexanes) provided the title compound: LCMS m/z 275.0 [M+H]+; 1H NMR (500 MHz, CDCl3) δ 13.43 (s, 1H), 8.74 (d, J=5.5 Hz, 1H), 7.98 (d, J=8.0 Hz, 1H), 7.76 (app d, J=5.5 Hz, 2H), 7.06 (t, J=8.0 Hz, 1H).

Provenance & Evidence