1,3-Dibromo-5,5-dimethylhydantoin → 5-Bromo-1,4-dimethyl-6-decyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a solution of 286 mg (0.99 mmol) of 1,4-dimethyl-6-decyl-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine in 4 mL of chloroform was added 143 mg (0.50 mmol) of 1,3-dibromo-5,5-dimethylhydantoin in portions at 0° C. The reaction mixture was stirred at 0° C. for 30 min. The reaction was quenched by the addition of 5 mL of sat aq NaHCO3. The mixture was extracted with chloroform and the combined organic layer was washed with brine and dried over MgSO4. The concentrated residue was purified by flash chromatography on a silica gel column (20 1.7 cm). Elution with 100:1 hexanes/ethyl acetate gave the product as a yellow oil: yield 342 mg (94%); silica gel TLC Rf 0.7 (8:1:1 hexanes/ethyl acetate/methanol); 1H NMR (CDCl3) δ 0.87 (t, 3H, J=6.8 Hz), 1.25-1.39 (m, 16H), 1.66 (quint, 2H, J=7.2 Hz), 2.17 (s, 3H), 2.77 (t, 2H, J=8.0 Hz), 2.83-2.87 (m, 5H) and 3.40 (t, 2H, J=8.0 Hz); 13C NMR (CDCl3) δ 14.1, 19.5, 22.7, 25.2, 28.7, 29.4, 29.54, 29.59, 29.64, 29.64, 31.9, 33.0, 38.1, 52.4, 110.9, 120.4, 141.1, 156.8 and 161.8; mass spectrum, m/z 366.2 and 268.2 (M)+ (theoretical 366.2 and 368.2); mass spectrum (APCI), m/z 367.1747 and 369.1673 (M+H)+ (C19H32N2Br requires 367.1749 and 369.1728).

Provenance & Evidence