Potassium Phosphate, Tribasic → HCID 57918478, compound

Participants

Reaction Steps

To a round bottomed flask were added 2-[(6-chloropyrimidin-4-yl)amino]-1-phenylethanol (62.4 mg, 0.25 mmol), 3-trifluoromethylphenyl boronic acid (71.2 mg, 0.38 mmol), K3PO4 (106.1 mg, 0.5 mmol), Pd(OAc)2 (8.4 mg, 0.013 mmol) and 1,1′-bis(di-tert-butylphosphino)-ferrocene (5.9 mg, 0.013 mmol). The flask was then evacuated, backfilled with N2, and charged with 1,4-dioxane (2.5 mL). The reaction mixture was heated at reflux for 2.5 h, before cooling to rt, diluting with EtOAc (15 mL), washing with water (2×10 mL), drying, and concentrating to dryness. The crude residue was purified (FCC) to yield the title compound (35.7 mg, 40%). MS (ESI): mass calcd. for C19H16F3N3O, 359.1; m/z found, 360.2 [M+H]+. 1H NMR (CD3OD): 8.50 (s, 1H), 8.23 (s, 1H), 8.15 (d, J=7.8 Hz, 1H), 7.78 (d, J=8.1 Hz, 1H), 7.69 (t, J=7.8 Hz, 1H), 7.44 (d, J=7.3 Hz, 2H), 7.37-7.33 (m, 2H), 7.28-7.24 (m, 1H), 6.96 (s, 1H), 4.93-4.90 (m, 1H), 3.79-3.69 (m, 1H), 3.61 (dd, J=13.6, 7.8 Hz, 1H).

Provenance & Evidence