5-Fluoro-1-(2-oxiranylmethyl)-1H-indole → HCID 9800520, compound

HRID 1532621Notes

Reaction equation

HRID 1532621 reaction equation
[CH2:1]([N:5]1[C:13]2[C:8](=[CH:9][C:10]([F:14])=[CH:11][CH:12]=2)[CH:7]=[CH:6]1)[CH:2]1[O:4][CH2:3]1.[NH:15]1[CH:20]=[CH:19][CH:18]([C:21]2[C:29]3[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=3)[NH:23][CH:22]=2)[CH2:17][CH2:16]1>>[F:14][C:10]1[CH:9]=[C:8]2[C:13](=[CH:12][CH:11]=1)[N:5]([CH2:1][CH:2]([OH:4])[CH2:3][N:15]1[CH2:16][CH:17]=[C:18]([C:21]3[C:29]4[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:19][CH2:20]1)[CH:6]=[CH:7]2

Participants

3

Reactant 2

HCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indoleHCID 21184334HCID 21184334, compound

Product 1

HCID 9800520HCID 9800520, compoundYield 78%

Procedure

A methanolic solution of 1-N-glycidyl-5-fluoroindole (0.52 g, 3.0 mmole) from example 1 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 light yellow colored solid (0.91 g, 78% yield). Treatment with a 0.25 M ethanolic solution of fumaric acid (0.5 equivalents) gave the required salt 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-f2cdf2e8115b4d7ea761f941baf72bc6
Source dataset
uspto-grants-2001_03
Patent number
US06204274B1

Reaction notes

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