Diisopropylamine → Ethyl 2-(tert-butyl(3-(3-(thiazol-5-yl)prop-2-ynyloxy)propyl)amino)-2-oxoacetate

Participants

Reaction Steps

A solution of 300 mg of 7f, 330 mg of 5-bromothiazole, 300 μl of diisopropyl amine and 200 μl of a 1M solution of tributyl phosphine in toluene, in 4 ml of degassed dioxane was charged with 21 mg of PdCl2 (benzonitrile)2 and 10 mg of CuI. The mixture was stirred under nitrogen atmosphere for 16 hr. The mixture was diluted with 30 ml of 5% NH4Cl and was extracted with ethyl acetate. The organic layer was washed with water, dried, concentrated and the residue was chromatographed over silica gel, using a gradient of heptane/ethyl acetate (1/1) as eluent, to provide 270 mg of N-tert-butyl-N-[3-(3-thiazol-5-yl-prop-2-ynyloxy)-propyl]oxalamic acid ethyl ester 8a, as colorless oil. Rf (heptane/ethyl acetate 1/1) 0.40.

Provenance & Evidence