1-Bromo-4-fluorobenzene → HCID 67005978, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(1H-indol-5-yl)-2,2-dimethyl-3-phenylpropanoic acid (Example 101(d), 31 mg, 0.11 mmol), 1-bromo-4-fluorobenzene (0.014 mL, 0.13 mmol), copper(I) iodide (4 mg, 0.02 mmol), potassium carbonate (50 mg, 0.36 mmol), trans-1,2-diaminocyclohexane (0.01 mL, 0.08 mmol), tetrabutylammonium iodide (18 mg, 0.05 mmol), and dioxane (0.6 mL) was stirred at 110° C. for 24 h. Concentration and purification using reverse phase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA) gave 3-(1-(4-fluorophenyl)-1H-indol-5-yl)-2,2-dimethyl-3-phenylpropanoic acid (24 mg, 0.062 mmol, 56% yield) as a liquid.

Provenance & Evidence