2,4,6-Trimethylpyridine → HCID 56970896, compound

Participants

Reaction Conditions

Reaction Steps

In a 100 mL round bottomed flask was placed 4-[4-(4-chlorophenyl)-4,5,6,7-tetrahydro-1-benzothien-2-yl]pyridine (821 mg, 2.52 mmol) and then dissolved in acetonitrile (10 mL) and 1,4-dioxane (10 mL). Then γ-Collidine (1.5 mL, 11 mmol) was added. To the mixture were added freshly prepared suspension of potassium persulfate (2.96 g, 10.9 mmol) and Copper(II) sulfate pentahydrate (278 mg, 1.11 mmol) in water (20 mL). The resulting mixture was stirred 6 h at 80° C. After stirring was continued for additional 1.5 h at the same temperature no increase in product formation was observed. The mixture was allowed to cool to rt and then was diluted with water (50 mL) and then extracted with EtOAc (50 mL×2). The combined organic phase was washed with freshly prepared 10% aqueous NaHSO3 (50 mL), saturated aqueous solution of NaHCO3 (50 mL), brine (50 mL), dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated under reduced pressure. The residue was purified by pre-packed silica gel (24 g) column chromatography eluted with a 30% to 100% EtOAc/hexane to yield title compound (568 mg; 66.3%) as a colorless crystalline solid.

Provenance & Evidence