Ammonium Chloride → HCID 54212301, 화합물

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To a solution of 4-(3-cyclopentyloxy-4-methoxyphenyl)-4-ethynyl-cyclohexan-1-one (0.22 g, 0.7 mmol) and 2-bromo-5-cyanothiophene (0.13 g, 0.7 mmol) in triethylamine (5 mL) under an argon atmosphere were added tetrakis(triphenylphosphine)palladium(0) (0.034 g, 4%) and copper(I) iodide (0.007 g, 6%), and the mixture was heated at 85°-90° C. for 2 h. Ammonium chloride was added and the mixture was extracted three times with dichloromethane, was dried (magnesium sulfate) and was evaporated. Purification by flash chromatography, eluting with 2:8 ethyl acetate:hexanes, provided 4-(2-cyanothien-5-ylethynyl)-4-(3-cyclopentyloxy-4-methoxyphenyl)cyclohexan-1-one (0.06 g, 18%). This was combined with product (0.017 g) obtained in a second, similar reaction and was triturated from dichloromethane-hexanes to provide a white solid, mp 106°-107° C. Anal. (C25H25NO3S.0.5 H2O) calcd: C, 70.07; H, 6.11; N, 3.27; found: C, 70.15; H, 5.84; N, 3.32.

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