Cesium carbonate → 2-({5-Chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl]amino)-N-methylbenzamide

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To a 10 mL sealable tube was added 2-[(2,5-dichloro-4-pyridinyl)amino]-N-methylbenzamide (95 mg, 0.321 mmol), 1,5-dimethyl-1H-pyrazol-4-amine (35.7 mg, 0.321 mmol), BINAP (20 mg, 0.032 mmol), cesium carbonate (314 mg, 0.964 mmol), and palladium(II) acetate (7.21 mg, 0.032 mmol) in 1,4-dioxane (5 mL). The reaction vessel was sealed and heated at 150° C. for 1 hr. The reaction mixture was purified using a prep HPLC (0.1% formic acid, 5 to 95% water:acetonitrile). Fractions were combined and evaporated. 2-({5-Chloro-2-[(1,5-dimethyl-1H-pyrazol-4-yl)amino]-4-pyridinyl}amino)-N-methylbenzamide (16 mg, 0.037 mmol, 11.38% yield) was isolated as yellow oil LCMS (M+H)+=371.1; 1H NMR (400 MHz, MeOD) ppm 2.17 (s, 3 H) 2.91 (s, 3 H) 3.78 (s, 3 H) 6.47 (s, 1 H) 7.13-7.24 (m, 1 H) 7.40 (s, 1 H) 7.46-7.57 (m, 2 H) 7.67 (dd, J=7.83, 1.26 Hz, 1 H) 7.82 (s, 1 H).

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