Potassium Carbonate → HCID 58056431, compound

Participants

Reaction Conditions

Reaction Steps

Into a 50 mL oven dried round bottom flask, 3-[1-(3-Bromo-2-methyl-benzenesulfonyl)-5-fluoro-1H-indol-3-yl]-propionic acid methyl ester (5, 52.062 mg, 1.1459E-4 mol), 4-trifluoromethoxy-phenyl boronic acid (6, 35.397 mg, 1.7189E-4 mol) and Tetrakis(triphenylphosphine)palladium(0) (13.24 mg, 1.146E-5 mol) were combined. A volume of 0.3 mL of 1N K2CO3 was added and the reaction was heated to 110° C. for 90 minutes. TLC analysis showed co-elution of product and starting material. Ethyl acetate was added and washed 5× with saturated sodium bicarbonate. The organic layer was dried over MgSO4, filtered and concentrated at reduced pressure. The crude material was purified using prep plate chromatography (7:3 hexane:ethyl acetate) to provide the desired compound (40 mg isolated, 65% yield). 1H NMR consistent with compound structure. MS(ESI) [M+H+]+=536.1 (calculated 535.51).

Provenance & Evidence