Reacción #1583834

Ecuación de reacción

methyl[(2-chloro-5-iodo-phenyl)methyl]carbamate

product

methyl[(2-chloro-5-iodo-phenyl)methyl]carbamate

ethynyltrimethylsilane

triphenylphosphine

→

title compound

methyl N-[[2-chloro-5-[2-(trimethylsilyl)ethynyl]-phenyl]methyl]carbamate

Disolventes

tetrahydrofuran

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   ConcentraciónThe reaction mixture was concentrated onto silica gel (7 g)
2. 2
   Otropurified by medium pressure liquid chromatography (0 to 25% gradient of ethyl acetate in hexanes as eluant)

Procedimiento

A mixture methyl[(2-chloro-5-iodo-phenyl)methyl]carbamate (i.e. the product of Step B) (3.0 g, 9.2 mmol), ethynyltrimethylsilane (1.94 mL, 13.8 mmol), bis(triphenylphosphine)palladium(II) dichloride (0.032 g, 0.05 mmol), copper(I) iodide (0.018 g, 0.09 mmol), triphenylphosphine (0.024 g, 0.09 mmol) in tetrahydrofuran (18 mL) and triethylamine (18 mL) was stirred at room temperature for 30 minutes. The reaction mixture was concentrated onto silica gel (7 g) and then purified by medium pressure liquid chromatography (0 to 25% gradient of ethyl acetate in hexanes as eluant) to provide the title compound as an oil (1.37 g).

Fuente