Cesium carbonate → 2-[(2,5-dichloro-4-pyridinyl)amino]-N-(methyloxy)benzamide

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Reaction Conditions

Reaction Steps

Palladium acetate (0.071 g, 0.32 mmol) was added under a nitrogen atmosphere to 2-amino-N-methoxybenzamide (1.32 g, 7.94 mmol) in dioxane (80 mL) containing 2,5-dichloro-4-iodopyridine (2.176 g, 7.94 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.276 g, 0.48 mmol) and cesium carbonate (5.18 g, 15.89 mmol). The resulting suspension was heated at 80° C. for 18 hours and then at 85° C. for a further 24 hours. The mixture was filtered through Celite and then concentrated in vacuo. The residue was diluted with MeOH and then loaded onto an SCX column. The mixture was eluted first with MeOH and then with a 7N solution of NH3 in MeOH. Fractions containing product were combined and then evaporated. The residue was triturated with Et2O to leave 2-[(2,5-dichloropyridin-4-yl)amino]-N-methoxybenzamide (0.823 g, 33% yield); 1H NMR spectrum: (300 MHz, DMSO) δ 3.66 (3H, s), 7.02 (1H, s), 7.26 (1H, m), 7.38 (1H, m), 7.56-7.64 (2H, m), 8.27 (1H, s), 9.66 (1H, s), 11.88 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+=311.93 and 313.96 and 315.92.

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