Cesium carbonate → [4-({3-[3-Methyl-8-(Trifluoromethyl)Quinolin-4-yl]Phenoxy}Methyl)Phenyl]Acetic Acid

Participants

Reaction Conditions

Reaction Steps

3-[3-Methyl-8-(trifluoromethyl)quinolin-4-yl]phenol (1.13 g, 3.73 mmol) and 4-bromomethylphenylacetic acid (1.02 g, 4.47 mmol) in CH2Cl2 (60 mL) is treated with Cs2CO3 (4.86 g, 14.9 mmol) and the reaction is stirred overnight. The solvent is removed and the residue dissolved in THF and 2N aq NaOH. After heating at 70° C. for 1 h, the reaction is cooled and the layers separated. The aqueous layer is further extracted with ethyl acetate. The combined organics are dried (Na2SO4) and concentrated. The residue is chromatographed eluting with 20:80 ethyl acetate:hexane and then 5:95 methanol:methylene chloride to afford the title product.

Provenance & Evidence