Sodium Carbonate → 4-Chloro-7-fluoro-3-methyl-2-(2-methylpyridin-3-yl)quinoline

Participants

Reaction Steps

To a stirred solution of 2,4-dichloro-7-fluoro-3-methylquinoline (400 mg, 1.74 mmol) in 1,4-dioxane:water (5 mL:1 mL) was added PdCl2(PPh3)2 (122 mg, 0.17 mmol), sodium carbonate (553 mg, 5.22 mmol) and 2-methyl-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine. The reaction was heated at reflux overnight. After this time the reaction was diluted with EtOAc (100 mL) and water (50 mL). The separated organic layer was dried over MgSO4, filtered and evaporated in vacuo. Column chromatography (hexane:EtOAc, 1:0 to 1:1) gave 4-chloro-7-fluoro-3-methyl-2-(2-methylpyridin-3-yl)quinoline.

Provenance & Evidence