Cesium carbonate → 2-[(2,5-Dichloro-4-pyridinyl)amino]-N-methylbenzamide

Participants

Reaction Conditions

Reaction Steps

Palladium(II) acetate (0.393 g, 1.75 mmol) was added to 2,5-dichloro-4-iodopyridine (12 g, 43.81 mmol), 2-amino-N-methylbenzamide (6.58 g, 43.81 mmol), cesium carbonate (28.6 g, 87.63 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (1.521 g, 2.63 mmol) in dioxane (600 mL) under an atmosphere of nitrogen. The resulting suspension was heated at 80° C. for 18 hours, allowed to cool to room temperature and then filtered. The filtrate was evaporated and the residue triturated with CH2Cl2 to leave 2-[(2,5-dichloropyridin-4-yl)amino]-N-methylbenzamide (6.306 g, 48% yield). The CH2Cl2 solution was evaporated and the residue triturated with CH2Cl2 to leave a second crop of 2-[(2,5-dichloropyridin-4-yl)amino]-N-methylbenzamide (1.87 g, 14% yield); 1H NMR spectrum: (300 MHz, DMSO) δ 2.78 (2H, d), 7.19-7.21 (2H, m), 7.54-7.60 (2H, m), 7.73 (1H, d), 8.28 (1H, s), 8.70 (1H, d), 10.41 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+=296.0 and 298.0 and 300.0.

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