Ethyl Acetate → 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamide

Participants

Reaction Steps

A solution of tetrabutylammonium fluoride (1 M) in THF was added dropwise to a solution of N-[1-(tert-butyl-diphenyl-silanyloxymethyl)-1-methyl-prop-2-ynyl]-2-(3-ethynyl-quinolin-6-yloxy)-2-methylsulfanyl-acetamide (1.49 g) at 0° C. The reaction mixture was allowed to warm up to room temperature, stirred for 1.5 h and then poured onto a mixture of ethyl acetate and brine. The two layers were separated and the aqueous layer was extracted thrice with ethyl acetate. The organic layers were combined, washed once with brine and then dried over sodium sulphate. After filtration and concentration under reduced pressure 2.47 g of crude material was isolated as a yellow oil which was purified by flash chromatography on silica gel (hexane/ethyl acetate) to provide 2-(3-ethynyl-quinolin-6-yloxy)-N-(1-hydroxymethyl-1-methylprop-2-ynyl)-2-methylsulfanyl acetamide as a white solid (0.646 g, m.p.=149-150° C.) which was used directly in Stage 6 described below.

Provenance & Evidence