Potassium Carbonate → HCID 118005536, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 4-chloro-6-(hydroxy(1-methyl-1H-imidazol-5-yl)(6-(trifluoromethyl)pyridin-3-yl)methyl)-2-methoxyquinolin-3-yl trifluoromethanesulfonate (70 mg, 0.12 mmol, Intermediate 11: step g), (4-(methylsulfonyl)phenyl)boronic acid (35 mg, 0.18 mmol), PdCl2(dppf) (9 mg, 0.012 mmol) and K2CO3 (16 mg, 0.12 mmol) was sparged with nitrogen three times. To this mixture was added 1,4-dioxane (2 mL) and water (0.3 mL) and the suspension purged with nitrogen. The resulting solution was heated to 65° C. for 15 hours. The reaction was allowed to cool to room temperature and concentrated to dryness. The residue was dissolved in DMSO, filtered and purified by reverse-phase HPLC (acetonitrile/water+TFA). The acidic fractions were neutralized by diluting with EtOAc and washing with saturated aqueous NaHCO3 followed by water. The organics were dried (MgSO4), filtered and concentrated to dryness to provide the title compound. 1H NMR (400 MHz, CD3OD) δ 8.79-8.76 (m, 1H), 8.24-8.20 (m, 1H), 8.08-8.05 (m, 2H), 8.05-8.01 (m, 1H), 7.96-7.93 (m, 1H), 7.84 (d, J=8.3 Hz, 1H), 7.76-7.72 (m, 2H), 7.65-7.62 (m, 2H), 6.35 (s, 1H), 4.00 (s, 3H), 3.49 (s, 3H), 3.20 (s, 3H); MS (ESI): mass calcd. for C28H22ClF3N4O4S, 602.1; m/z found, 603.2 [M+H]+.

Provenance & Evidence