HCID 10442179, compound → HCID 9951324, compound

HRID 1532625Notes

Reaction equation

HRID 1532625 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:14]1[CH:19]=[CH:18][CH:17]([C:20]2[C:28]3[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=3)[NH:22][CH:21]=2)[CH2:16][CH2:15]1>>[N:5]1([CH2:1][CH:2]([OH:4])[CH2:3][N:14]2[CH2:15][CH:16]=[C:17]([C:20]3[C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[NH:22][CH:21]=3)[CH2:18][CH2:19]2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6]1

Participants

3

Reactant 2

HCID 10442179HCID 10442179, compoundHCID 21184334HCID 21184334, compound

Product 1

HCID 9951324HCID 9951324, compoundYield 47.6%

Procedure

A methanolic solution of 1-N-glycidylindole (0.52 g, 3.0 mmole) from example 4 and 3-(4-tetrahydropyridinyl)indole (0.59 g, 3.0 mmole) was refluxed under nitrogen for 24 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 (0.53 g, 47% 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-cb44ea4541114734aba5d92400839ba4
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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