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

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Reaction Steps

A solution of 390 mg of 11d, 290 mg of 5-bromothiazole, 400 μl of diisopropyl amine, 40 mg of PdCl2(PheCN)2, 20 mg of CuI and 300 μl of a 1M solution of tri-tert-butyl phosphine (in toluene) in 4 ml of degassed dioxane, was stirred under N2 for 16 hr. The mixture was poured into 20 ml of 5% aq. NH4Cl solution and extracted with ethyl acetate. The organic layer was dried, concentrated and the product was chromatographed over silica gel, using a gradient of heptane/ethyl acetate, to give 450 mg of 11e as a colorless oil; Rf 0.40 (heptane/ethyl acetate 1/1);

Provenance & Evidence