Phenylacetylene → HCID 68470303, compound

Participants

Reaction Steps

Pd(PhCN)2Cl2 (0.03 eq.) and CuI (0.02 eq.) were added to a dry septum-capped vial, which was then sparged with argon and charged with ethyl 4-bromo-5-[(tert-butoxycarbonyl)amino]thiophene-2-carboxylate (prepared as described in example 14, step 4) (1 M solution in dioxane), DIEA (1.2 eq.), P(t-Bu)3 (0.06 eq., 0.8 M solution in dioxane) and phenylacetylene (1.2 eq.). The reaction was stirred overnight at RT, then diluted with AcOEt and filtered trough a small pad of silica gel. The filtrate was concentrated giving a residue that was purified by flash chromatography on silica gel (1:5 AcOEt/petroleum ether) to afford the title compound (96%) as a solid.

Provenance & Evidence