N-bromobutanimide → 5-Bromo-6-ethylpyridin-2-amine

Participants

Reaction Steps

A 0° C. solution of 6-ethylpyridin-2-amine (3.37 g, 27.6 mmol) in CHCl3 (30 mL) was treated portion-wise with NBS (4.91 g, 27.6 mmol) over 30 min, stirred for 45 min, then concentrated to dryness. The residue was treated with EtOAc (8 mL), filtered to remove solids and purified via silica gel chromatography (EtOAc/Hex) to afford 5-bromo-6-ethylpyridin-2-amine (3.79 g, 68%). 1H NMR (400 MHz, DMSO-d6): δ 7.43 (d, J=8.6 Hz, 1 H), 6.21 (d, J=8.7 Hz, 1 H), 6.03 (s, 2 H), 2.61 (q, J=7.5 Hz, 2 H), 1.11 (t, J=7.5 Hz, 3 H);

Provenance & Evidence