Trimethylsilylacetylene → Thiazole, 2-[(trimethylsilyl)ethynyl]-

Participants

Reaction Steps

A solution of 2-Bromothiazole (Aldrich, 5.0 g, 30.5 mmol), ethynyl-trimethyl-silane (Aldrich, 3.0 g, 30.5 mmol), PdCl2(PPh3)2 (Aldrich, 500 mg, 0.71 mmol) and CuI (Aldrich, 400 mg, 1.52 mmol) in THF (20 mL) was treated with TEA (5 mL) at room temperature for 20 min. The reaction was heated at 60 for 4 hours. The solid was filtered off through a pad of celite and the filtrate was concentrated to give yellow solid, which was then purified by silica gel column on a CombiFlash® system using hexanes and ethyl acetate (from 10% ethyl acetate to 100% ethyl acetate) to afford the title compound as yellow oil.

Provenance & Evidence