2-amino-1-(4-methoxybenzyl)-4,5,6,7-tetrahydro-1H-indole-3-carbonitrile → 4-Amino-9-(4-methoxyphenyl)methyl-2-phenyl-5,6,7,8-tetrahydro-9H-pyrido[2,3-b]indole-3-carboxylic acid, methyl ester

HRID 1710051Notes

Reaction equation

HRID 1710051 reaction equation
[NH2:1][C:2]1[N:3]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=2)[C:4]2[CH2:5][CH2:6][CH2:7][CH2:8][C:9]=2[C:10]=1[C:11]#[N:12].[CH3:22][O:23][C:24](=[O:35])[CH:25]=[CH:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29](OC)[CH:28]=1>>[NH2:12][C:11]1[C:10]2[C:9]3[CH2:8][CH2:7][CH2:6][CH2:5][C:4]=3[N:3]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:2]=2[N:1]=[C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:25]=1[C:24]([O:23][CH3:22])=[O:35]

Participants

3

Reactant 2

HCID 27640692-amino-1-(4-methoxybenzyl)-4,5,6,7-tetrahydro-1H-indole-3-carbonitrileHCID 54105512Methyl m-methoxycinnamate

Product 1

HCID 867441814-Amino-9-(4-methoxyphenyl)methyl-2-phenyl-5,6,7,8-tetrahydro-9H-pyrido[2,3-b]indole-3-carboxylic acid, methyl esterYield 73%

Procedure

Using a procedure similar to Description 6, the title compound (D12) was prepared in 73% yield from 2-amino-3-cyano-1-(4-methoxyphenyl)methyl-4,5,6,7-tetrahydroindole (D5) and methyl-3-methoxycinnamate.

Sources & evidence

ORD record
ord-6e1174aec19e46e1bf19fcc893a1e1a3
Source dataset
uspto-grants-1990_08
Patent number
US04952584

Reaction notes

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