5-Methyl-2-thiophenecarboxaldehyde → Methyl 1,2,3,4-tetrahydro-1-(5-methyl-2-thienyl)-9h-pyrido [3,4-b]indole-3-carboxylate

HRID 365798Notes

Reaction equation

HRID 365798 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C@H:4]([CH2:6][C:7]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)[NH2:5].[CH3:17][C:18]1[S:22][C:21]([CH:23]=O)=[CH:20][CH:19]=1>>[CH3:23][C:21]1[S:22][C:18]([CH:17]2[C:8]3[NH:9][C:10]4[C:15]([C:7]=3[CH2:6][CH:4]([C:3]([O:2][CH3:1])=[O:16])[NH:5]2)=[CH:14][CH:13]=[CH:12][CH:11]=4)=[CH:19][CH:20]=1

Participants

3

Reactant 2

HCID 616635-Methyl-2-thiophenecarboxaldehydeHCID 77980L-Tryptophan, methyl ester

Product 1

HCID 3879449Methyl 1,2,3,4-tetrahydro-1-(5-methyl-2-thienyl)-9h-pyrido [3,4-b]indole-3-carboxylate

Procedure

The same method but starting from racemic tryptophan methyl ester and 5-methyl-2-thiophenecarboxaldehyde gave the cis and trans isomers of the title compound.

Sources & evidence

ORD record
ord-1eea5f76951d40d8ae956b84ca35f332
Source dataset
uspto-grants-2000_10
Patent number
US06127542

Reaction notes

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