Cesium carbonate → HCID 67466579, compound

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of 2,5-difluoro-4-(5-iodopyrimidin-4-yloxy)benzenamine (0.23 g, 0.659 mmol) in DMF (5 mL) was added 1-methyl-pyrazole-4-boronic acid pinacol ester (0.206 g, 0.988 mmol), cesium carbonate (0.644 g, 1977 mmol) in water (2 mL) and Pd(PPh3)4 (0.076 g, 0.066 mmol) and the mixture was stirred at 80° C. under an argon atmosphere for 1 hour. Water was added and the solution was extracted with EtOAc (3×). The organics were washed with 5% aqueous lithium chloride solution and brine, and then dried over MgSO4. The organics were filtered and concentrated under reduced pressure. The residue was treated with small amount of EtOAc and Et2O. The solid was collected by filtration to obtain 2,5-difluoro-4-(5-(1-methyl-1H-pyrazol-4-yl)pyrimidin-4-yloxy)benzenamine (0.18 g, 90% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.02 (s, 1H), 8.54 (s, 1H), 8.30 (s, 1H), 8.09 (s, 1H), 7.21 (m, 1H), 6.69 (m, 1H), 5.42 (s, 2H), 3.89 (s, 3H); MS (ESI) m/z: 304.1 (M+H+).

Provenance & Evidence