Cesium carbonate → 6-[4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-ylmethoxy]-2-methyl-3-nitro-pyridine

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of [4-Isopropyl-2-(2-trifluoromethoxy-phenyl)-2H-pyrazol-3-yl]-methanol (2.0 g, 6.66 mmol) in degassed toluene (22 mL) is added 6-Chloro-2-methyl-3-nitro-pyridine (1.15 g, 6.66 mmol), cesium carbonate (3.25 g, 9.99 mmol), 2-(Di-t-butylphosphino)-1,1′-binapthyl (332 mg, 0.833 mmol, 12.5 mol %), and palladium (II) acetate (150 mg, 0.666 mmol, 10 mol %). The reaction mixture is heated to 70° C. overnight. The reaction mixture is filtered through a pad of Celite®, is concentrated under reduced pressure, and is chromatographed (0% to 20% EtOAc/Hex) to yield the title compound (2.73 g, 94%). 1H NMR (400 MHz, CDCl3) δ 8.22 (d, 1H, J=8.8 Hz), 7.64 (s, 1H), 7.52 (dd, 1H, J=7.8, 1.7 Hz), 7.49-7.44 (m, 1H), 7.41-7.34 (m, 2H), 6.51 (d, 1H, J=9.2 Hz), 5.35 (s, 2H), 3.05 (sept, 1H, J=7.0 Hz), 2.72 (s, 3H), 1.29 (d, 6H, J=7.0 Hz).

Provenance & Evidence