HCID 15524201, compound → HCID 9887307, compound

HRID 1532624Notes

Reaction equation

HRID 1532624 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:16]1[CH:21]=[CH:20][CH:19]([C:22]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[NH:24][CH:23]=2)[CH2:18][CH2:17]1>>[NH:24]1[C:25]2[C:30](=[CH:29][CH:28]=[CH:27][CH:26]=2)[C:22]([C:19]2[CH2:20][CH2:21][N:16]([CH2:3][CH:2]([OH:4])[CH2:1][N:5]3[C:13]4[C:8](=[C:9]([O:14][CH3:15])[CH:10]=[CH:11][CH:12]=4)[CH:7]=[CH:6]3)[CH2:17][CH:18]=2)=[CH:23]1

Participants

3

Reactant 2

HCID 15524201HCID 15524201, compoundHCID 21184334HCID 21184334, compound

Product 1

HCID 9887307HCID 9887307, compoundYield 60.6%

Procedure

A methanolic solution of 1-N-glycidyl-4-methoxyindole (0.6 g, 3.0 mmole) from example 2 and 3-(4-tetrahydropyridinyl)indole (0.59 g, 3.0 mmole) was refluxed under nitrogen for 15 hours. The reaction mixture was concentrated in vacuo and the product purified by flash silica gel chromatography (ethyl acetate) to afford the titled compound as a yellow colored solid (0.73 g, 60% yield). Treatment with a 0.25M ethanolic solution of fumaric acid (0.5 equivalents) gave the required product as a yellow colored solid. The product was recrystallized from ethanol.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe product purified by flash silica gel chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4c5dfb116bda4e28949a152c8abd2054
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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