Reaction #1583834

Reaction equation

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

Solvents

tetrahydrofuran

triethylamine

Conditions

Workup

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

Procedure

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).

Source