2-Aminothiazole → 2,6-dichloro-N-(2-(thiazol-2-ylamino)pyridin-4-yl)benzamide

Participants

Reaction Conditions

Reaction Steps

A 25 mL microwave tube containing N-(2-bromopyridin-4-yl)-2,6-dichlorobenzamide (0.21 g, 0.61 mmol), 2-aminothiazole (92 mg, 0.92 mmol), Pd2(dba)3 (56 mg, 0.061 mmol), Cs2CO3 (0.4 g, 1.22 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (Xantphos, 71 mg, 0.122 mmol), and dioxane (8 mL) was degassed and then charged with N2 (3×). The resulting mixture was heated at 80° C. overnight. After cooling, 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 (56.4 mg, yield: 25%). 1HNMR: (DMSO-d6, 400 MHz): 611.26 (s, 1H), 11.13 (s, 1H), 8.21 (d, J=6.0 Hz, 1H), 7.61-7.50 (m, 4H), 7.36 (d, J=3.6 Hz, 1H), 7.11 (q, J=1.6, 6.0 Hz, 1H), 6.98 (d, J=3.6 Hz, 1H). LCMS (ESI) m/z: 364.8 [M+H+]

Provenance & Evidence