Cesium carbonate → HCID 86655135, compound

Participants

Reaction Conditions

Reaction Steps

Palladium(II) acetate (0.066 g, 0.29 mmol) was added to 2,5-dichloro-4-iodopyridine (2 g, 7.30 mmol), 2-amino-N-methoxy-N-methylbenzamide (1.316 g, 7.30 mmol), cesium carbonate (4.76 g, 14.60 mmol) and 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (0.254 g, 0.44 mmol) in dioxane (100 mL) under an atmosphere of nitrogen. The resulting suspension was heated at 80° C. for 18 hours and then allowed to cool to room temperature. The mixture was filtered and the filtrate evaporated. The residue was purified by chromatography on silica, eluting with a gradient of 0-5% MeOH in CH2Cl2. Fractions containing product were combined and evaporated to afford 2-[(2,5-dichloropyridin-4-yl)amino]-N-methoxy-N-methylbenzamide (0.775 g, 33% yield); 1H NMR spectrum: (300 MHz, DMSO) δ 3.18 (3H, s), 3.48 (3H, s), 6.61 (1H, d), 7.34-7.40 (1H, m), 7.45-7.47 (1H, m), 7.54-7.57 (2H, m), 8.19 (1H, s), 8.47 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+=326.0 and 328.0 and 330.0.

Provenance & Evidence