Water → HCID 67240006, compound

Participants

Reaction Steps

To a stirred suspension of ethyl 2,4-dichloro-1,5-naphthyridine-3-carboxylate (1.0 g, 3.69 mmol) in acetonitrile:water (7 mL:2 mL) was added Pd (PPh3)4 (0.426 g, 0.369 mmol), 3-fluorophenylboronic acid (0.568 g, 4.06 mmol) and sodium carbonate (0.782 g, 7.38 mmol) and the reaction was heated at reflux for 6 h. After this time the reaction was cooled to rt and partitioned between EtOAc (80 mL) and water (30 mL). The separated organic layer was dried over MgSO4, filtered and concentrated in vacuo. The mixture was purified by column chromatography on silica gel using a gradient from 1:0 to 4:1 of hexane:EtOAc to give ethyl 4-chloro-2-(3-fluorophenyl)-1,5-naphthyridine-3-carboxylate as a white solid: LC-MS (ESI) m/z 331.0 [M+H]+.

Provenance & Evidence