Cesium carbonate → 2,4-Difluoro-5-(pyrimidin-5-yl)benzaldehyde

Participants

Reaction Conditions

Reaction Steps

A mixture of bis(triphenylphosphine)palladium(II) chloride (0.56 g, 0.80 mmol), pyrimidin-5-ylboronic acid (0.99 g, 8.0 mmol), 5-bromo-2,4-difluorobenzaldehyde (0.88 g, 3.98 mmol), cesium carbonate (2.59 g, 7.96 mmol) in DME (13 mL), EtOH (7 mL) and water (7 mL) was heated at 100° C. for 45 min, and the crude reaction mixture was subjected to HPLC separation eluting with 0-100% A/B (A: 95% H2O/5% MeCN, 10 MM NH4OAc; B: 5% H2O/95% MeCN, 10 mM NH4OAC over 30 min period to give the title compound as a white solid (450 mg, 51% yield). 1H NMR (500 MHz, CHLOROFORM-d) δ 10.40-10.33 (m, 1H), 9.28 (s, 1H), 8.94 (d, J=1.2 Hz, 2H), 8.06 (dd, J=8.4, 7.8 Hz, 1H), 7.15 (t, J=9.9 Hz, 1H), 10.37 (s, 1H).

Provenance & Evidence