Citric Acid → HCID 178427848, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of (E)-5-(3-(4-bromophenyl)-3-(4-fluoro-2-methylphenyl)-1-(hydroxyimino)propyl)-1-methylpyridin-2(1H)-one (0.1 g, example 224) in dioxane (1 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium dichloromethane adduct (CAS RN: [95464-05-4]) (9.21 mg), 4-(1H-tetrazol-5-yl)phenylboronic acid (64.3 mg, CAS RN: [179942-55-3]), water (0.65 mL) and aqueous 2M sodium carbonate solution (338 μL) and the reaction mixture was heated for 23 hours at 80° C. The reaction mixture was poured on 10% aqueous citric acid solution and ethyl acetate and the layers were separated. The aqueous layer was extracted twice with ethyl acetate. The combined organic layers were dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography using a MPLC system (20 g silica gel column, CombiFlash Companion, Isco Inc.) eluting with a gradient of dichloromethane:methanol (100:0 to 75:25). The product was purified a second time by preparative HPLC (phenomenex gemini column) with a gradient of acetonitrile:water (containing 0.5% formic acid) (10:90 to 98:2) to yield the title compound containing 10% of the corresponding Z isomer as as a white foam, MS (ESI+): m/z=509.21 [M+H]+.

Provenance & Evidence