2-Vinylquinoline → 8-Chloro-2,3,4,5-tetrahydro-2-[2-(2-quinolinyl)ethyl]-1H-pyrido-[4,3-b]indole

HRID 980316Notes

Reaction equation

HRID 980316 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][NH:13][CH2:14][C:5]=3[C:4]=2[CH:3]=1.[CH:15]([C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[N:18]=1)=[CH2:16].C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][CH2:12][N:13]([CH2:16][CH2:15][C:17]4[CH:26]=[CH:25][C:24]5[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=5)[N:18]=4)[CH2:14][C:5]=3[C:4]=2[CH:3]=1

Participants

4

Reactant 3

HCID 698752-VinylquinolineHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 9049708-Chloro-2,3,4,5-tetrahydro-1H-pyrido(4,3-b)indole

Product 1

HCID 137724548-Chloro-2,3,4,5-tetrahydro-2-[2-(2-quinolinyl)ethyl]-1H-pyrido-[4,3-b]indole

Procedure

The title compound was prepared following the procedure of Example 2 with the exception that 8-chloro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole was used instead of 8-fluoro-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole and 2-vinylquinoline was used instead of 2-vinylpyridine. The product was converted to the dihydrochloride salt; mp 187°-190° C.

Sources & evidence

ORD record
ord-441a28ad3a6e45588118df93f72bff82
Source dataset
uspto-grants-1987_01
Patent number
US04636563

Reaction notes

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