Acetic Acid → HCID 86728251, compound

Participants

Reaction Steps

N′,N′-dimethylethane-1,2-diamine (39 mg, 0.440 mmol) and CH3COOH (26 mg, 0.440 mmol) were added to the mixture of 2-bromo-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7(8H)-one (100 mg, 0.293 mmol) in 1,2-dichloroethane (2 mL). The mixture was stirred at room temperature for 20 minutes. Then NaBH(OAc)3 (93 mg, 0.440 mmol) was added to the mixture. The mixture was stirred at room temperature for 2 hours. The mixture was then quenched with saturated NaHCO3 (30 mL) and extracted with ethyl acetate (15 mL×3). The organic layer was washed with brine (20 mL), dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified using p-TLC (dichloromethane:MeOH=1:1) to provide N1-(2-bromo-7,8-dihydro-6H-benzo[2,3][1,5]oxazocino[5,4-a]indol-7-yl)-N2,N2-dimethylethane-1,2-diamine. 1H-NMR (CDCl3, 400 MHz) δ 7.51˜7.56 (m, 2H), 7.42 (s, 1H), 7.29˜7.32 (m, 1H), 7.16˜7.18 (m, 1H), 7.06 (t, J=7.2 Hz, 1H), 6.85 (d, J=8.8 Hz, 1H), 6.56 (s, 1H), 3.86˜4.32 (m, 4H), 2.81˜3.03 (m, 5H), 2.59 (s, 6H). MS (M+H)+: 414/416.

Provenance & Evidence