Triethylamine → 4-Phenyl-5-trimethylsilanylethynyl-thiazol-2-ylamine

Participants

Reaction Steps

Under a stream of Ar the above prepared 5-iodo-4-phenyl-thiazol-2-ylamine (1.60 g, 5.29 mmol) was dissolved in 30 mL of acetonitrile and treated successively with triethylamine (2.09 mL, 3 eq.), Cul (0.096 g, 0.1 eq.), (Ph3P)2PdCl2 (0.353 g, 0.1 eq. and ethynyltrimethylsilane (2.09 mL, 3 eq.). The flask was closed with a septum and allowed to stir for 15 h at ambient temperature. 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=8/2) yielded finally 1.075 g of the title compound as brown foam. MS (ISP): 273.3 [M+H]+.

Provenance & Evidence