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 1940563노트

반응식

HRID 1940563 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-c03eb31f40684b118450e1d9e006812a
출처 데이터셋
uspto-grants-1997_12
특허 번호
US05700809

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