反应 #66082

反应方程式

product

7-[(6-methylpyridin-3-yl)ethynyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

→

title compound

7-[(Z)-2-(6-methylpyridin-3-yl)vinyl]-3,4,5,6-tetrahydro-1H-2,5-ethanoazepino[4,3-b]indole

溶剂

methanol

反应条件

后处理

1. 1
   其他The reaction flask was purged with nitrogen
2. 2
   其他then purged with hydrogen
3. 3
   其他The flask was purged with nitrogen
4. 4
   过滤the reaction mixture was filtered
5. 5
   浓缩The filtrate was concentrated under vacuum
6. 6
   其他the residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)]

实验过程

The product of Example 3 (100.9 mg, 0.308 mmol) was dissolved in methanol (5 mL). Lindlar catalyst (5% Pd on CaCO3 poisoned with lead, Aldrich, 9.8 mg) was added to the reaction mixture. The reaction flask was purged with nitrogen then purged with hydrogen, and the mixture was stirred under hydrogen (1 atm) at room temperature for 3 hours. The flask was purged with nitrogen and the reaction mixture was filtered. The filtrate was concentrated under vacuum, and the residue was purified by reverse-phase HPLC [Waters XBridge™ RP18 column, 5 μm, 30×100 mm, flow rate 40 mL/minute, 20-99% gradient of methanol in buffer (0.1 M aqueous ammonium bicarbonate, adjusted to pH 10 with ammonium hydroxide)] to afford the title compound: 1H NMR (300 MHz, methanol-d4) δ ppm 2.01-2.10 (m, 4H), 2.41 (s, 3H), 2.97-3.13 (m, 3H), 3.21-3.26 (m, 2H), 26 (s, 2H), 6.69 (d, J=12.2 Hz, 1H), 6.88-6.90 (m, 2H), 6.99 (d, J=11.9 Hz, 1H), 7.04 (d, J=8.1 Hz, 1H), 7.21-7.26 (m, 1H) 7.44 (dd, J=8.2, 2.0 Hz, 1H), 8.16 (d, J=2.4 Hz, 1H); MS (APCI) m/z 330 (M+H)+.

来源