Dichloromethane → HCID 66729579, compound

Participants

Reaction Steps

In a microwave tube a solution of N-[3-(4-Bromo-1-ethyl-1H-pyrazol-3-yl)-2-fluoro-phenyl]-2,5-difluoro-N-methoxy-methyl-benzenesulfonamide (prepared as described in Example 1) (420 mg, 0.833 mmol) in DME/H2O 9:1 (10 mL) was degassed by bubbling argon for 5 minutes, 4-pyridinyl boronic acid pinacol ester (256 mg, 1.249 mmol, 1.5 eq) was then added, followed by cesium carbonate (543 mg, 1.666 mmol, 2 eq) and Pd(dppf)Cl2.CH2Cl2 (68 mg, 0.083 mmol, 0.1 eq). The mixture was irradiated in the microwave oven at 100° C. for 30 minutes. It was then filtered over a Celite pad, which was washed thoroughly with AcOEt. The filtrate was washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4 and evaporated to dryness. The crude product was purified by chromatography on silica gel (DCM/MeOH 97:3) and 370 mg (88%) of N-[3-(1-Ethyl-4-pyridin-4-yl-1H-pyrazol-3-yl)-2-fluoro-phenyl]-2,5-difluoro-N-methoxymethyl-benzenesulfonamide were obtained as a white solid. HPLC (254 nm): Rt: 6.10 min; 1H NMR (DMSO-d6) Shift: 8.39 (s, 1H), 8.35-8.41 (m, 2H), 7.57-7.65 (m, 1H), 7.45-7.56 (m, 3H), 728-7.39 (m, 2H), 7.04-7.08 (m, 2H), 5.01 (s, 2H), 4.22 (q, J=7.2 Hz, 2H), 3.28 (s, 3H), 1.46 (t, J=7.3 Hz, 3H); HRMS (ESI) calcd for C24H22F3N4O3S [M+H]+ 503.1359. found 503.1342.

Provenance & Evidence