Cesium carbonate → 6-bromo-N-(4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)-4-methylpyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

To a flask was added 2-bromo-4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridine (329 mg, 0.953 mmol), 2-bromo-4-methyl-6-aminopyridine (178 mg, 0.953 mmol), Pd(OAc)2 (21.4 mg, 0.095 mmol), Xantphos (83 mg, 0.143 mmol), and Cs2CO3 (621 mg, 1.91 mmol), and the mixture was vacuum-purged with argon 3 times. Degassed 1,4-Dioxane (3.8 mL) was added and the reaction was heated to 100° C. for 30 min. after which time the reaction was cooled and diluted with EtOAc (20 mL). The reaction was filtered then dry loaded onto silica and purified by silica gel chromatography using a gradient solvent system of 30-60% EtOAc/Hexanes. Concentration of the product-containing fractions yielded 6-bromo-N-(4-(1-(4-methoxybenzyl)-1H-1,2,3-triazol-4-yl)pyridin-2-yl)-4-methylpyridin-2-amine (255 mg, 59%) as a tan solid. MS ESI calcd for C21H19BrN6O [M+H]+ 451, found 451.

Provenance & Evidence