Potassium Carbonate → HCID 18971807, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of (1.0 g, 5.71 mmol, 1.0 eq) 3-carbomethoxy indole, (2.21 g, 7.42 mmol, 1.3 eq) (±)-1-methoxy-2-exo-norbornyloxy-4-bromobenzene (30.7 mg, 0.107 mmol, 0.2 eq) cuprous bromide, and (866 mg, 6.27 mmol, 1.1 eq) potassium carbonate in 15 ml of 1-methyl-2-pyrrolidinone was heated to 150° C. for 24 hours. The reaction mixture was cooled, diluted with 350 ml of ethyl acetate and 350 ml of H2O, and the layers separated. The aqueous layer was extracted twice with ethyl acetate. The ethyl acetate extracts were combined, washed twice with H2O, once with brine, dried over Na2SO4 and concentrated in vacuo to give a light brown oil. Silica gel chromatography eluting with 20% ethyl acetatehexane gave 1.05 g, 47%, of a white foamy solid. M.P.: 120°-122° C. Elemental Analysis Calc'd for C24H25NO4 : Calc'd: C, 73.64; H, 6.44; N, 3.58. Found: C, 73.70; H, 6.37; N, 3.59.

Provenance & Evidence