1,2-Dimethoxyethane → tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate

Participants

Reaction Conditions

Reaction Steps

tert-Butyl ((5-bromo-1-((3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 7b (770 mg, 1.5 mmol), 2-(cyclohex-1-en-1-yl)-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (394 mg, 1.4 mmol, prepared by a known method disclosed in “Journal of the American Chemical Society, 2002, 124(27), 8001-8006”), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium (53 mg, 0.07 mmol) and potassium carbonate (401 mg, 2.9 mmol) were successively added to 15 mL of a mixed solvent of ethylene glycol dimethyl ether and water (V/V=3:1), then the reaction solution was heated up to 100° C. and stirred for 10 h. 15 mL of water were added, and the reaction solution was extracted with ethyl acetate (50 mL×4). The organic phases were combined, dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography with elution system C to obtain the title product tert-butyl ((5-(cyclohex-1-en-1-yl)-1-((3-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)sulfonyl)-1H-pyrrol-3-yl)methyl)(methyl)carbamate 7c (554 mg, a light yellow oil) in 72% yield.

Provenance & Evidence