Cesium carbonate → 2-(2-chloro-5-fluoropyridin-4-ylamino)-N-methylbenzamide

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Cesium carbonate (651 mg, 2.00 mmol) was added to a mixture of 2-amino-N-methylbenzamide (150 mg, 1.00 mmol), 2-chloro-5-fluoro-4-iodopyridine (257 mg, 1.00 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (35 mg, 0.06 mmol) and palladium(II) acetate (9 mg, 0.04 mmol) in dioxane (10 mL) under an atmosphere of nitrogen and the resulting suspension was heated at 80° C. for 24 hours. The mixture was filtered through Celite and the residue washed with CH2Cl2 (20 mL). The filtrate was evaporated and the residue was then dissolved in CH2Cl2 (40 mL) and washed sequentially with a saturated solution of NaHCO3 (25 mL), water (25 mL), and finally with a saturated solution of NaCl (25 mL). The organic layer was dried over MgSO4 and then evaporated to leave a solid. The solid was triturated in CH2Cl2 to afford 2-(2-chloro-5-fluoropyridin-4-ylamino)-N-methylbenzamide (231 mg, 83% yield); 1H NMR spectrum (300.132 MHz, d6 DMSO+d4 Acetic acid): δ 2.76 (3H, s), 7.19 (1H, m), 7.22 (1H, d), 7.50-7.58 (2H, m), 7.71 (1H, dd), 8.19 (1H, d); Mass spectrum: m/z (ESI+) (M+H)+=280.0 and 282.0.

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