Hydrochloric Acid → HCID 89853996, compound

Participants

Reaction Conditions

Reaction Steps

Into a 20 mL microwave vial were added benzyl 1-(4-bromo-1H-pyrazol-1-yl)cyclopropanecarboxylate (421 mg, 1.31 mmol), cyclopropyltrifluoroborate potassium salt (582 mg, 3.93 mmol), 1,1′-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) complex with dichloromethane (42.5 mg, 0.052 mmol) and cesium carbonate (1710 mg, 5.24 mmol). The vial was sealed, evacuated and backflushed with nitrogen two times followed by the addition of tetrahydrofuran (7 mL). The reaction mixture was stirred at 80° C. for 18 h. The solvent was removed under reduced pressure and to the residue was added water (100 mL) and ethyl acetate. The layers were separated and the aqueous layer was extracted with ethyl acetate (2×). After the second extraction an emulsion formed that was cleared with the addition of brine, ethyl acetate and aqueous hydrochloric acid (1N). The aqueous layers were extracted again with ethyl acetate (2×), the solvent was removed under reduced pressure and the residue was purified via flash chromatography (0-100% ethyl acetate in heptanes) to afford benzyl 1-(4-cyclopropyl-1H-pyrazol-1-yl)cyclopropanecarboxylate (91 mg, 25%). MS (ES+) (M+H) 283.3; LCMS retention time: 3.38 minutes (Method L).

Provenance & Evidence