N-bromobutanimide → 2-Amino-5-bromo-3-fluoropyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 3-fluoro-pyridin-2-ylamine (example C.29 step 2) (3 g, 26.8 mmol) in acetonitrile (50 mL) at 0° C. was added NBS (4.77 g, 26.8 mmol) and the mixture was stirred at 23° C. for 2 h. Poured on ice with sat. NaHCO3-sol., extracted thrice with AcOEt, dried over Na2SO4. Removal of the solvent in vacuum left a residue, which was purified by silica gel column chromatography with heptane/AcOEt 3:1 to give the title compound as a brown solid (3.1 g, 60%). MS (ISP) 191 [(M+H)+], 193 [(M+2+H)+].

Provenance & Evidence