6-Phenyl-1,2,3,4-tetrahydroisoquinoline → 3-(6-phenyl-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl-1H-pyrrolo[2,3-b]pyridine

HRID 1940563Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1940563
[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][NH:12][CH2:11][CH2:10]3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH2:20][C:21]1[C:29]2[C:24](=[N:25][CH:26]=[CH:27][CH:28]=2)[NH:23][CH:22]=1)C>C1(C)C=CC=CC=1>[C:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[CH2:13][N:12]([CH2:20][C:21]2[C:29]4[C:24](=[N:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=2)[CH2:11][CH2:10]3)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

4

Edukt 2

HCID 323966-Phenyl-1,2,3,4-tetrahydroisoquinolineHCID 53835493-(Dimethylaminomethyl)-7-azaindole

Produkt 1

HCID 214630023-(6-phenyl-1,2,3,4-tetrahydroisoquinolin-2-yl)methyl-1H-pyrrolo[2,3-b]pyridineAusbeute 17 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A mixture of 6-phenyl-1,2,3,4-tetrahydroisoquinoline (prepared by the method of L. N. Pridgen, J. Heterocyclic Chem. 1980, 17, 1289) (0.5 g, 2.38 mmol) and 3-dimethylaminomethyl-1H-pyrrolo[2,3-b]pyridine (0.4 g, 2.28 mmol) in toluene (5 ml) was heated at reflux under nitrogen for 18 h. The mixture was allowed to cool and the crystallised product collected. Recrystallisation from ethyl acetate afforded the title compound (0.13 g, 17%), m.p. 211°-213° C.; (Found: C, 80.15; H, 6.30; N, 12.32. C23H21N3.0.3H2O requires C, 80.11; H, 6.31; N, 12.18%); δH (DMSO-d6) 2.73 (2H, br s, CH2CH2Ph), 2.87 (2H, br s, NCH2CH2), 3.61 (2H, s, ArCH2N), 3.83 (2H, s, NCH2Ph), 7.02 (1H, dd, J 7.8, 4.6 Hz, 5-H), 7.18 (1H, d, J 3.2 Hz, 2-H), 7.30-7.45 (6H, m, ArH), 7.60 (2H, d, J 7.6 Hz, ArH), 8.05 (1H, d, J 7.6 Hz, 4-H), 8.20 (1H, dd, J 6.1, 1.4 Hz, 6-H), and 11.48 (1H, br s, NH); m/z (CI+, NH3) 340 (M+1)+.

Aufarbeitung

  1. customprepared by the method of L
  2. temperatureat reflux under nitrogen for 18 h
  3. temperatureto cool
  4. customthe crystallised product collected
  5. customRecrystallisation from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-c03eb31f40684b118450e1d9e006812a
Quelldatensatz
uspto-grants-1997_12
Patentnummer
US05700809

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