Potassium Carbonate → 5-(7-Chloro[1,6]naphthyridin-3-yl)-2-fluoro-4-methylaniline

Participants

Reaction Conditions

Reaction Steps

Sparge a solution of 3-bromo-7-chloro-1,6-naphthyridine (0.5 g, 2.053 mmol) and 2-fluoro-4-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)aniline (0.516 g, 2.053 mmol) in dioxane (15 mL) with Ar, add a solution of K2CO3 (0.568 g, 4.11 mmol) in H2O (3 mL), followed by Pd(PPh3)4 (0.237 g, 0.205 mmol), heat at 75° C. for 8 h, then cool to RT. Add H2O, extract with EtOAc (2×), wash the combined organics with brine, dry over Na2SO4, concentrate to dryness and purify via silica gel chromatography (EtOAc/Hex) to afford the title compound (470 mg, 80%) as an off-white solid. MS(ESI) m/z: 288.1 (M+H+).

Provenance & Evidence