Ethanol → HCID 57437893, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-chlorophenyl)-N-cyclohexyl-5-propyl-pyrazole-4-carboxamide (Intermediate #22) (159 mg, 0.46 mmol), Molybdenum hexacarbonyl (61 mg, 0.23 mmol), Herrmann's catalyst (Trans-Di-Mu-Acetatobis[2-(Di-O-Tolylphosphino)Benzyl]dipalladium(II), 22 mg, 0.02 mmol), DMAP (113 mg, 0.92 mmol), DIPEA (161 μL, 0.92 mmol), Fu's salt (Tri-(T-Butyl)Phosphonium Hydrogen tetrafluoroborate Salt, 27 mg, 0.09 mmol), Dioxane (2 mL), Ethanol (2 L) were mixed into a microwave tube. The reaction mixture was then heated at 150° C. for 1 hour by microwave. LC-MS showed complete conversion to the product. The solvent was evaporated under reduced pressure and the reaction mixture extracted with EtOAc (2×25 mL), washed with water (10 mL), 2N HCl (10 mL) and brine (10 mL). The organic phase was dried over MgSO4 and evaporated under reduced pressure to give a black gum. The residue was purified by column chromatography (12 g silicycle column, gradient: 1:0 to 1:1 hexane/EtOAc) and appropriate fractions combined and concentrated in vacuo to yield the desired compound as a white solid (130 mg, 74%).

Provenance & Evidence