3-Bromopyridine → N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine

Participants

Reaction Steps

To a small reaction vessel was added palladium acetate (1.5 mg, 7micromol), tris-(ortho-toluyl)phospine (4.2 mg, 14micromol) and 3-bromopyridine (22 mg, 0.13 mmol) as a solution in acetonitrile (1.5 mL) in one portion. The mixture was stirred for 5 minutes at room temperature under an atmosphere of nitrogen gas and then intermediate (b), N-Boc-(R)-2-(3-vinylbenzyl)morpholine (0.083 g, 0.27 mmol) was added as a solution in acetonitrile (1.5 mL). The reaction vessel was then subjected to microwave power to heat the reaction to 140° C. for 5 minutes and then cooled to room temperature. The crude reaction was added directly to a silica column and the mixture washed with solvent (10-60% ethyl acetate:isohexane). The desired material was concentrated in vacuo and purified by column chromatography (silica; 50% ethyl acetate: isohexane) to obtain the desired coupling product intermediate (a), N-Boc-(R)-2-(3-(2-(3-pyridinyl)vinyl)-benzyl)morpholine as a colorless oil (30 mg, 57%).

Provenance & Evidence