Cesium carbonate → 2,6-dichloro-N-(2-(3-fluoropyridin-2-ylamino)pyridin-4-yl)benzamide

Participants

Reaction Steps

A 25 mL microwave tube containing N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (100 mg, 0.29 mmol), 3-fluoropyridin-2-amine (42 mg, 0.38 mmol), Pd2(dba)3 (8 mg, 0.008 mmol), Cs2CO3 (190 mg, 0.58 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 4 mg, 0.003 mmol), and dioxane (15 mL) was degassed and then charged by N2 (3×). The resulting mixture was then irradiated in a microwave reactor at 130° C. for 30 min. The mixture was diluted with dioxane (20 mL) and filtered through Celite. The filtrate was concentrated under reduced pressure and the residue was purified by reverse-phase HPLC (Gemini, 200 mm×25 mm, gradient: CH3CN/0.05% NH3.H2O, 50-80%, 10 min) to afford the desired product (377 mg, yield: 45%). 1H NMR (400 MHz, DMSO) δ 11.07 (s, 1H), 8.98 (s, 1H), 8.28-8.01 (m, 3H), 7.70-7.48 (m, 4H), 7.37 (s, 1H), 7.01 (s, 1H). LCMS (ESI) m/z: 378.5 [M+H+].

Provenance & Evidence