反应详情

1.5 mmol of 9-(2-morpholino-2-oxoethyl)-9H-pyrido[3,4-b]indole-1-carbaldehyde, 1.5 mmol of (S)-5,6,7,8-tetrahydroquinolin-8-amine, and 3.00 mmol of sodium triacetoxyborohydride in 20 ml dichloromethane were stirred for 2 hours at room temperature, then reaction was quenched with saturated sodium bicarbonate solution. Organic layer was dried over magnesium sulfate, filtered off, and evaporated. Desired product was purified with column chromatography using dichloromethane:methanol:NH4OH (9:1:0.1) solvent system (85% yield). ESI+ MS: m/z (rel intensity) 456.2 (100, [M+H]+). 1H-NMR (400 MHz, CDCl3): δ 8.38 (d, 1H, J=4.8 Hz), 8.36 (d, 1H, J=1.6 Hz), 8.12 (d, 1H, J=7.6 Hz), 7.92 (d, 1H, J=5.6 Hz), 7.55 (dt, 1H, J=1.2, 8.0 Hz), 7.37 (d, 1H, J=7.6 Hz), 7.29 (q, 2H, J=4.8 Hz), 7.07 (q, 1H, 4.8 Hz), 6.11 (d, 1H, J=18.0 Hz), 5.74 (d, 1H, J=17.6 Hz), 4.46 (d, 1H, J=12.0 Hz), 4.33 (d, 1H, J=12.0 Hz), 4.00 (t, 1H, J=5.6 Hz), 3.82-3.76 (m, 1H), 3.73-3.60 (m, 6H), 3.55-3.50 (m, 1H), 2.78 (t, 2H, J=6.4 Hz), 2.18-2.08 (m, 1H), 1.96-1.66 (m, 4H).

1. customreaction
2. customwas quenched with saturated sodium bicarbonate solution
3. dry with materialOrganic layer was dried over magnesium sulfate
4. filtrationfiltered off
5. customevaporated
6. customDesired product was purified with column chromatography