Cesium carbonate → HCID 68095362, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 6-chloro-2-(2-chlorophenyl)-1,7-naphthyridine (50 mg, 0.2 mmol), cyclopropanecarboxamide (27 mg, 0.32 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (16 mg, 0.03 mmol), palladium acetate (4 mg, 0.02 mmol), and cesium carbonate (118 mg, 0.36 mmol) in 1,4-dioxane (1 mL) was heated at 90° C. for 3 hours. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and washed with water (100 mL). The organic layer was separated, dried over sodium sulfate, filtered, and evaporated in vacuo to afford a residue that was purified by reverse phase HPLC (5-85% acetonitrile in water with 0.1% formic acid over 14 min) to afford the title compound as an off-white solid (15 mg, 20%). 1H NMR (400 MHz, CDCl3) δ 9.28 (s, 1H), 8.58 (s, 1H), 8.28 (s, 1H), 8.16 (d, J=8.6 Hz, 1H), 7.90 (d, J=8.6 Hz, 1H), 7.71 (m, 1H), 7.53 (m, 1H), 7.42 (m, 2H), 1.64 (m, 1H), 1.21-1.14 (m, 2H), 1.01-0.91 (m, 2H). LCMS (Method E): RT=4.970 min, M+H+=324.1.

Provenance & Evidence