Sodium Carbonate → 4-[5-(1-Morpholin-4-yl-ethyl)-furan-2-yl]-benzoic acid

Participants

Reaction Conditions

Reaction Steps

4-[1-(5-bromo-furan-2-yl)-ethyl]-morpholine (0.54 mmol) was taken up in 7 ml toluene and 4-carboxymethylphenylboronic acid (0.54 mmol) was added as a solution in 0.7 ml of EtOH. 12 mi of 2M aqueous Na2CO3 solution was added, followed by Pd(PPh3)4 (0.054 mmol). Reaction was stirred at 70° C. for 17 h under a nitrogen atmosphere and then cooled to room temperature and extracted with DCM (×2). Combined organic layers were washed with brine, concentrated in vacuo and the residue purified by flash chromatography (silica, 20-50% EtOAc in hexane). This fumished the pure 4-[5-(1-Morpholin-4-yl-ethyl)-furan-2-yl]-benzoic acid methyl ester as a powdery grey solid: m/z in MS ES+=316 [M+H]+, 0.08 mmol, 15% yield.

Provenance & Evidence