Sodium Carbonate → HCID 89649473, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-benzyloxy-4-bromo-1-fluoro-benzene [CAS: 1036724-54-5](1250 mg, 4.45 mmol) in MeCN (40 mL) and water (10 mL) was added 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1 h-pyrazole (925.18 mg, 4.45 mmol), sodium carbonate (1414.18 mg, 13.34 mmol) and bis(triphenylphosphine)palladium (II) dichloride (157.92 mg, 0.2200 mmol). The reaction was then heated at 100° C. for 4 hours. The reaction mixture was poured into EtOAc (100 mL) and aq NaOH (0.5M, 200 mL). The organics were separated, and washed with brine (75 mL), dried over MgSO4, filtered and concentrated in vacuo. The residue was then purified over silica (25 g, SNAP cartridge), eluting with between 0% and 40% EtOAc in isohexane. Fractions containing the desired product were combined and concentrated in vacuo to give 4-(3-benzyloxy-4-fluoro-phenyl)-1-methyl-pyrazole (D78) (760 mg, 2.5575 mmol, 57.6% yield) as a colourless oil;

Provenance & Evidence