N-bromobutanimide → HCID 67328691, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution containing 213 mg (0.60 mmol) of 4-methoxy-6-(10-(methoxymethoxy)decyl)-N,N-dimethylpyridin-2-amine in 5 mL of acetonitrile were added 107 mg (0.60 mmol) of N-bromosuccinimide. The reaction mixture was stirred at 23° C. protected from light for 3 h. The reaction mixture was poured into 50 mL of satd. aq. sodium bicarbonate and extracted two 50-mL portions of ethyl acetate. The combined organic layer was washed with one 50-mL portion of brine, dried (MgSO4) and concentrated under diminished pressure. The residue was purified by chromatography on a silica gel column (3×10 cm). Elution with 4:1 hexanes-ethyl acetate afforded the expected product as a yellowish oil: yield 114 mg (44%); silica gel TLC Rf 0.45 (4:1 hexanes-ethyl acetate); 1H NMR (CDCl3) δ 1.29 (br m, 12H), 1.56 (quint, 2H, J=7.2 Hz), 1.68 (quint, 2H, J=7.2 Hz), 2.55 (dd, 2H, J=7.6, 7.6 Hz), 3.03 (s, 6H), 3.33 (s, 3H), 3.48 (t, 2H, J=6.8 Hz), 3.85 (s, 3H), 4.59 (s, 2H) and 5.76 (s, 1H); 13C NMR (CDCl3) δ 26.17, 28.08, 29.40, 29.47, 29.51, 29.57, 29.65, 29.72, 37.31, 38.05, 38.05, 55.02, 55.65, 67.87, 86.47, 96.35, 97.29, 158.80, 159.11 and 162.60; mass spectrum (APCI), m/z (M+H)+431.1913 (C20H36N2O3Br requires 431.1909).

Provenance & Evidence