Indole → HCID 21906898, compound

HRID 1246936Notes

Reaction equation

HRID 1246936 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[C:10](Cl)(=[O:14])[C:11]([Cl:13])=[O:12].C1COCC1>C(OCC)C>[ClH:13].[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([C:10](=[O:14])[C:11]([Cl:13])=[O:12])=[CH:2]1

Participants

5

Reactant 3

HCID 798IndoleHCID 8028TetrahydrofuranHCID 65578Oxalyl chloride

Product 1

HCID 21906898HCID 21906898, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Indole, intermediate A1, is treated with oxalyl chloride, in a solvent such as THF or diethyl ether, to provide the 3-indolylglyoxalyl chloride hydrochloride salt, which is further treated with NaOMe in MeOH, to yield the methyl 3-indolylglyoxylate, intermediate B1. A second indole, A1, is converted to the acetamide intermediate C1, by stirring A1 with NaH in DMF, followed by the addition of iodoacetamide. Intermediates B1 and C1 are suspended in THF and treated with 3 to 4 equivalents of a base such as KOtBu, to provide compound 1, which falls under the general class of 3-(indol-3-yl)-4-(1N-indolyl)-1H-pyrrole-2,5-diones.

Sources & evidence

ORD record
ord-58e8b6653cff465ab0d08b0715b3963a
Source dataset
uspto-grants-2006_10
Patent number
US07129250B2

Reaction notes

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