Cesium carbonate → HCID 66704216, compound

Participants

Reaction Conditions

Reaction Steps

To an ambient temperature solution of [5-isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-yl]-methanol (2.0 g, 6.64 mmol) in degassed toluene (22 mL) are added 6-chloro-2-methyl-3-nitro-pyridine (1.15 g, 6.64 mmol), cesium carbonate (3.25 g, 9.96 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 is filtered through a pad of diatomaceous earth. The filtrate is concentrated and the residue is chromatographed (SiO2 120 g, 0% to 20% EtOAc/Hexane to yield 6-[5-Isopropyl-3-(2-trifluoromethoxy-phenyl)-3H-[1,2,3]triazol-4-ylmethoxy]-2-methyl-3-nitro-pyridine (2.78 g, 96%). 1H NMR (400 MHz, CDCl3) δ 8.23 (d, 1H, J=8.8 Hz), 7.61-7.53 (m, 2H), 7.48-7.42 (m, 2H), 6.51 (d, 1H, J=8.8 Hz), 5.42 (s, 2H), 3.26 (sept, 1H, J=7.0 Hz), 2.71 (s, 3H), 1.43 (d, 6H, J=7.0 Hz).

Provenance & Evidence