Triethylamine → (4-Methyl-5-trimethylsilanylethynyl-thiazol-2-yl)-carbamic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

Under a stream of Ar the above prepared (5-iodo-4-methyl-thiazol-2-yl)-carbamic acid tert-butyl ester (0.913 g, 2.68 mmol) was dissolved in 17 mL of acetonitrile and treated successively with triethylamine (1.12 mL, 3 eq.), Cul (0.051 g, 0.1 eq.), (Ph3P)2PdCl2 (0.188 g, 0.1 eq.), and ethynyltrimethylsilane (1.11 mL, 3 eq.). The flask was closed with a septum and allowed to stir for 4 h at 32° C. The reaction mixture was then poured onto icewater/NH4Cl, twofold extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, and evaporated to dryness. Flash chromatography (SiO2, hexane/ethyl acetate=85/15) gave finally 0.592 g of the title compound as light brown foam.

Provenance & Evidence