Bromine → HCID 14761929, compound

Participants

Reaction Steps

To a stirred solution of 5-benzylpyridin-2-amine 2 (6.0 g, 32.3 mmol) in CH2C12 (100 mL) cooled to 0° C. was added bromine (5.1 g, 32.3 mmol) dropwise [Kelly, et al., J. Am. Chem. Soc. 112, 8024-8034 (1990)]. The bromine decolorized immediately and the mixture was left stirring for 30 min. The mixture was shaken with saturated NaHCO3 solution (100 mL), the organic layer was then dried over anhydrous Na2SO4, and distilled off to give a yellow residue which was purified by flash chromatography on silica gel (EtOAc:hexane, 3:7). Yield 7.3 g (86%), white solid, mp 110-111° C. 1H NMR (CDCl3, 500 MHz): δ 3.86 (s, 2H, CH2), 4.88 (bs, 2H, NH2), 7.19-7.35 (m, 5H, Ar—H), 7.50 (d, 1H, CH, J=1.5 Hz), 7.94 (d, 1H, CH, J=1.0 Hz). 13C NMR (CDCl3, 125 MHz): δ 37.7, 104.6, 126.4, 126.4, 128.1, 128.6, 128.6, 128.7, 140.2, 140.8, 146.7, 154.0; HRMS (M+H)+ calcd for C12H13BrN2 263.0184, found 263.0184.

Provenance & Evidence