3-Amino-2-bromopyridine → HCID 89930616, compound

Participants

Reaction Steps

A mixture of tert-butyl[(2S)-1-{[tert-butyl(diphenyl)silyl]oxy}but-3-yn-2-yl]carbamate (30, 144 mg, 0.340 mmol), 2-bromopyridin-3-amine (53 mg, 0.306 mmol) (or any other suitable halide or triflate ester) and bis(triphenylphosphine)palladium(II) dichloride (18 mg, 0.026 mmol) was dissolved in degassed dry TEA (1.2 mL, 8.61 mmol) and acetonitrile (0.6 ml), stirred for 5 minutes at room temperature and treated with copper(I) iodide (7 mg, 0.037 mmol). The final mixture was placed in a preheated oil bath at +52° C. and further stirred under N2 in the dark for 4.5 h, concentrated and submitted to purification through a chromatographic cartridge of silicagel (12 g) eluted with 0.5% to 12% MeOH in DCM (UV detection at 254 nm) to give title compound (157 mg, 99% yield) as a brown solid. MS: m/z=516.3 (MH+).

Provenance & Evidence