Cesium carbonate → HCID 46214778, compound

Participants

Reaction Conditions

Reaction Steps

A 20-mL microwave tube was charged with 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide (100 mg, 0.320 mmol), 1-ethyl-3-methyl-1H-pyrazol-5-amine (60.1 mg, 0.481 mmol), cesium carbonate (313 mg, 0.961 mmol), 1,4-dioxane (5.0 mL) and THF (1.0 mL). The reaction mixture was degassed by nitrogen for 10 min. (±)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene (19.95 mg, 0.032 mmol) and Palladium(II) acetate (3.60 mg, 0.016 mmol) in minimum amount of 1,4-dioxane were then added. The tube was sealed and reaction mixture was heated in microwave oven 160° C. for 40 min. The resulting suspension was cooled to room temperature and filtered through celite. The filtrate was evaporated to dryness and the crude reaction mixture was purified by reverse-phase HPLC to give the title compound as a solid (16 mg, 24% yield) MS: M(C19H21ClN6O2)=400.86, (M+H)+=401; 1H NMR (400 MHz, MeOD) δ ppm 7.92 (s, 1 H) 7.44-7.66 (m, 3 H) 7.11-7.25 (m, 1 H) 6.61 (s, 1 H) 5.99 (s, 1 H) 3.98 (q, J=7.3 Hz, 2 H) 3.80 (s, 3 H) 2.21 (s, 3 H) 1.32 (t, J=7.2 Hz, 3 H).

Provenance & Evidence