2-Bromothiazole → HCID 22618309, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 5-chloro-2-(3,5-di-t-butyl-4-hydroxy-benzyl)-7-ethynyl-benzoxazole (2.38 g, 6.0 mM), 2-bromothiazole (1.13 ml, 95%, 12 mM), bistriphenylphosphine)palladium(II) dichloride (21.1 mg, 30 uM), copper (I) iodide (1.2 mg, 6 uM) in triethylamine (12 ml) was heated at 90° C., under argon, for 3 hours. The triethylamine was removed in-vacuo and the residue dissolved in ether (70 ml) and water (30 ml). The organics were washed with 1N HCl (30 ml) and saturated sodium hydrogen carbonate (30 ml), dried (Na2SO4) and evaporated in-vacuo to give 2.86 g (100%) of crude thiazolylethynylbenzoxazole, which was purified by flash chromatography (SiO2 ; dichloromethane). The product was crystallized and recrystallized from methanol to give 1.43 g (50.4%) of the title compound (mp 137°-41° C.).

Provenance & Evidence