5-Fluoro-1-(2-oxiranylmethyl)-1H-indole → HCID 9800520、化合物

HRID 1532621ノート

反応式

HRID 1532621 の反応式
[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

参加物

3

反応物 2

HCID 155242005-Fluoro-1-(2-oxiranylmethyl)-1H-indoleHCID 21184334HCID 21184334、化合物

生成物 1

HCID 9800520HCID 9800520、化合物収率 78%

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-f2cdf2e8115b4d7ea761f941baf72bc6
出典データセット
uspto-grants-2001_03
特許番号
US06204274B1

反応ノート

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