Cesium carbonate → HCID 86655139, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2,5-dichloro-4-iodopyridine (0.56 g, 2.04 mmol), 2-amino-N-methyl-5-(4-methylpiperazin-1-yl)benzamide (0.508 g, 2.04 mmol), 9,9-dimethyl-4,5-s bis(diphenylphosphino)xanthene (0.071 g, 0.12 mmol), cesium carbonate (1.332 g, 4.09 mmol) and palladium(II) acetate (0.018 g, 0.08 mmol) was suspended in DMA (15 mL). The mixture was heated at 100° C. for 1 hour in a microwave reactor and then allowed to cool to room temperature. The mixture was loaded onto an SCX column and the product eluted first using MeOH and then with a 7M solution of NH3 in MeOH. Fractions containing product were combined and evaporated to afford 2-[(2,5-dichloropyridin-4-yl)amino]-N-methyl-5-(4-methylpiperazin-1-yl)benzamide as a DMA adduct (0.990 g); 1H NMR spectrum: (300 MHz, DMSO) δ 2.23 (3H, s), 2.44-2.50 (4H, m), 2.73 (3H, d), 3.16-3.21 (4H, m), 6.90 (1H, s), 7.10-7.14 (1H, m), 7.20 (1H, d), 7.40 (1H, d), 8.19 (1H, s), 8.58 (1H, d), 9.67 (1H, s); Mass spectrum: m/z (ESI+) (M+H)+=394.09.

Provenance & Evidence