Ethyl Acetate → 6-[2-Methoxy-4-(6-methylpyridin-3-ylcarbonyloxy)phenyl]-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline

Participants

Reaction Steps

6-(4-Hydroxy-2-methoxyphenyl)-5-(5-methylthiophen-2-ylcarbonyloxymethyl)-2,2,4-trimethyl-1,2-dihydroquinoline (Reference Compound No. 3-2, 32.5 mg, 0.0723 mmol) and 6-methylnicotinoic acid (15.7 mg, 0.114 mmol) were dissolved in N,N-dimethylformamide (1 mL), N,N-diisopropylethylamine (35 μL, 0.201 mmol) and O-(7-azabenzotriazol-1-yl)-N,N,N,N-tetramethyluronium hexafluorophosphate (38.3 mg, 0.101 mmol) were added thereto, and then the mixture was stirred at room temperature overnight. Ethyl acetate (20 mL) was added to the reaction mixture, and then the mixture was washed with water (20 mL) and saturated brine (20 mL) successively. After the organic layer was dried over anhydrous magnesium sulfate, the solvent was removed under reduced pressure. The obtained residue was purified by silica gel column chromatography (hexane-ethyl acetate) to give the titled compound (21.5 mg) as a gray amorphous product. (Yield 57%)

Provenance & Evidence