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

HRID 1710049Notes

Reaction equation

HRID 1710049 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].C(O/[C:25](/[CH3:32])=[CH:26]\[C:27]([O:29][CH2:30][CH3:31])=[O:28])C>C(O)C>[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:25]([CH3:32])[C:26]=1[C:27]([O:29][CH2:30][CH3:31])=[O:28]

Participants

4

Reactant 2

HCID 27640692-amino-1-(4-methoxybenzyl)-4,5,6,7-tetrahydro-1H-indole-3-carbonitrileHCID 5904488Ethyl 3-ethoxy-2-butenoate

Product 1

HCID 867441794-Amino-9-(4-methoxyphenyl)methyl-2-methyl-5,6,7,8-tetrahydro-9H-pyrido[2,3-b]indole-3-carboxylic acid, ethyl esterYield 64%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The title compound was prepared in 64% yield from 2-amino-3-cyano-1-(4-methoxyphenyl)methyl-4,5,6,7-tetrahydroindole (D5) and ethyl β-ethoxycrotonate in a procedure similar to Description 6. Product was obtained as beige crystals from ethanol.

Sources & evidence

ORD record
ord-fc2eccfcfca74c62a66ff209bddf6882
Source dataset
uspto-grants-1990_08
Patent number
US04952584

Reaction notes

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