Potassium Carbonate → HCID 66656356, compound

Participants

Reaction Conditions

Reaction Steps

4-Chloro-2-(3-nitro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazol-4-yl)phenol (500 mg, 1.544 mmol), 3-cyanophenylboronic acid (453 mg, 3.09 mmol), di-mu-chlorobis[5-chloro-2-[(4-chlorophenyl)(hydroxyimino)methyl]phenyl]palladium (II) dimer (63 mg, 0.0772 mmol), tri-tert-butylphosphonium tetrafluoroborate (45 mg, 0.154 mmol), potassium carbonate (426 mg, 3.09 mmol) and tetrabutyl ammonium hydroxyde solution (1M in MeOH, 0.31 mL, 0.31 mmol) were combined in a microwave vial. DMF (7.5 mL) was added and the vial was sealed. The mixture was heated at 130° C. for 1 hour under microwave irradiation and then partitioned between ethyl acetate (25 mL) and water (10 mL). The organic layer was separated and washed with brine (10 mL), dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified on silica gel by Biotage™ (10% to 80% EtOAc in heptane over 20 CV) to give the title compound (254 mg, 41%) as brown oil

Provenance & Evidence