Reaktionsgleichung
[CH2:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[CH2:4][CH:3]([C:14]([O:16][CH3:17])=[O:15])[NH:2]1)=[CH:12][CH:11]=[CH:10][CH:9]=3.[C:18]([Cl:26])(=O)[C:19]1C=CC=C[CH:20]=1.C(N(CC)CC)C.[CH2:34]1[CH2:38][O:37][CH2:36][CH2:35]1>>[Cl:26][C:18]1[CH:36]=[CH:35][C:34]([C:38]([N:2]2[CH:3]([C:14]([O:16][CH3:17])=[O:15])[CH2:4][C:5]3[C:13]4[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=4)[NH:7][C:6]=3[CH2:1]2)=[O:37])=[CH:20][CH:19]=1Komponenten
Versuchsvorschrift
A mixture of methyl 1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate (6.9 g, 30 mmol), benzoylchloride (4.2 g, 30 mmol) and triethylamine (4.8 mL) in anhydrous THF (150 mL) was refluxed for 9 h. It was concentrated and diluted with water. The solid precipitated was collected by filtration, the solid cake was washed successfully with water and hexane and dried to give methyl 2-(4-chlorobenzoyl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate, 9.0 g (82%); mp 243-244° C. (lit.19 mp 245-246° C.). 1H NMR (DMSO-d6) δ 3.10 (1H, m, CH2), 3.35 (1H, m, CH2), 3.55 and 3.65 (3H, s, COOMe), 4.41 and 5.18 (1H, d, J=17.4 Hz, NCH2), 4.51 and 4.64 (1H, d, J=16.4 Hz, NCH2), 4.88 and 5.82 (1H, d, J=5.4 Hz, CH), 6.96-6.99 (1H, m, ArH), 7.03-7.08 (1H, m, ArH), 7.25-7.32 (1H, m, ArH), 7.42-7.60 (5H, m, 5×ArH), 10.65 and 10.95 (1H, s, exchangeable NH).
Aufarbeitung
- temperaturewas refluxed for 9 h
- concentrationIt was concentrated
- additiondiluted with water
- customThe solid precipitated
- filtrationwas collected by filtration
- washthe solid cake was washed successfully with water and hexane
- customdried
Quellen und Nachweise
- ORD-Eintrag
- ord-4f942f0800fb45cabd9d6cba5683b246
- Quelldatensatz
- uspto-grants-2014_04
- Patentnummer
- US08703951B2
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