1,4-Dioxane → (S)-tert-butyl ((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate

Participants

Reaction Steps

To a microwave vial containing (S)-tert-butyl((3-bromopyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate (500 mg, 1.159 mmol) and a stir bar was added 1,4-dioxane (6 mL). To this solution was added tetrakis(triphenyl-phosphine)palladium(0) (67.0 mg, 0.058 mmol, 0.05 equiv.) and tributyl(prop-1-yn-1-yl)stannane (458 mg, 1.391 mmol, 1.2 equiv.). The vial was capped and irradiated in a microwave at 120° C. for 20 min. The vial was allowed to cool, diluted with hexanes (5 mL) and loaded directly to a normal phase silica gel column (80 g ISCO, 0 to 40% EtOAc in hexanes) to provide (S)-tert-butyl((3-(prop-1-yn-1-yl)pyridin-2-yl)(4-(trifluoromethyl)phenyl)methyl)carbamate as a white solid.

Provenance & Evidence