Potassium Carbonate → HCID 59627921, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-methyl-4-[(phenylmethyl)oxy]-1H-indole (R. A. Heacock et al. Canadian Journal of Chemistry, (1964), 42(3), 514) (617 mg, 2.60 mmol) in N-methyl-2-pyrrolidinone (10 mL) was added 4-bromo-2-fluorophenol (0.28 mL, 2.60 mmol), copper iodide (96 mg, 0.50 mmol) and potassium carbonate (867 mg, 6.28 mmol). The reaction mixture was heated in a Biotage Initiator™ Microwave Synthesizer at 190° C. for 3 hours. The mixture was filtered through a pad of Celite which was subsequently washed with ethyl acetate. The ethyl acetate solution was washed with water and then the aqueous layer re-extracted with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered and then concentrated in vacuo. The product was purified by silica gel chromatography eluting with 0-30% ethyl acetate in hexane to yield the title compound (D2) (147 mg).

Provenance & Evidence