Sodium Carbonate → HCID 89158091, compound

Participants

Reaction Conditions

Reaction Steps

4-Bromo-2-chloro-3,6-difluoroaniline (12.37 mmol, 3 g) and 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole-5-boronic acid pinacol ester (12.37 mmol, 3.44 g) were dissolved in DME. Bis(triphenylphosphine)palladium(II) chloride (0.619 mmol, 0.434 g) and sodium carbonate, 2 M solution (12.37 mmol, 1.311 g) were added. The reaction mixture was refluxed at 80° C. for 4 h and the stirring was continued at 50° C. overnight. The solvent was evaporated and the residue was extracted three times with EtOAc. The combined organics were washed with water and brine. The organics were dried, filtered and evaporated. The crude product was purified by flash chromatography. 1.935 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): δ 1.49-1.79 (m, 2H), 1.80-1.88 (m, 1H), 1.93-2.19 (m, 2H), 2.33-2.47 (m, 1H), 3.47-3.77 (m, 1H), 3.96-4.07 (m, 1H), 5.09-5.43 (m, 1H), 6.30-6.39 (m, 1H), 7.04-7.13 (m, 1H), 7.50-7.63 (m, 1H).

Provenance & Evidence