Cesium carbonate → Methyl 4-(8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate

Participants

Reaction Conditions

Reaction Steps

A suspension of 8-bromo-[1,2,4]triazolo[1, 5-a]pyridin-2-amine (2.8 g, 13.2 mmol, 1 equiv), methyl 4-iodobenzoate (3.4 g, 13 mmol, 1.0 equiv), cesium carbonate (8.4 g, 26 mmol, 2.0 equiv), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (763 mg, 1.32 mmol, 0.10 equiv), and palladium (II) acetate (300 mg, 1.32 mmol, 0.10 equiv) in dioxane (100 mL) was heated at 80° C. for 1 h. The reaction mixture was cooled to room temperature and diluted with dichloromethane (100 mL). The resulting solids were filtered and sequentially rinsed with water (3×50 mL) and methanol (2×20 mL). The solids were dried in vacuo to afford methyl 4-(8-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)benzoate (3.1 g). 1H NMR (400 MHz, DMSO-d6), δ: 10.42 (s, 1H), 8.87 (m, 1H), 7.93 (m, 1H), 7.92 (d, J=8.8 Hz, 2H), 7.77 (d, J=8.8 Hz, 2H), 7.00 (dd, J=7.4, 6.9 Hz, 1H), 3.81 (s, 3H).

Provenance & Evidence