反応 #70512

ord-c91fbd736325417ba00f180335ca975c

反応方程式

N#Cc1cccc(C(=O)N2CCC(c3c[nH]c4ccccc34)CC2)c1
3-[4-(1H-Indol-3-yl)-piperidine-1-carbonyl]-benzonitrile
[Na+].[OH-]
NaOH
CCCC[N+](CCCC)(CCCC)CCCC.[OH-]
tetrabutyl ammonium hydroxide
Fc1ccc(CBr)cc1
4-fluoro-benzyl bromide
N#Cc1cccc(C(=O)N2CCC(c3cn(Cc4ccc(F)cc4)c4ccccc34)CC2)c1
3-{4-[1-(4-Fluoro-benzyl)-1H-indol-3-yl]-piperidine-1-carbonyl}-benzonitrile

溶媒

反応条件

詳細条件
See reaction.notes.procedure_details.

後処理

  1. 1
    その他The layers are separated
  2. 2
    その他the organic solvent is removed under the reduced pressure
  3. 3
    その他purified by a silica gel flash column

実験手順

3-[4-(1H-Indol-3-yl)-piperidine-1-carbonyl]-benzonitrile (0.08 g, 0.24 mmol) is dissolved in 2 ml THF, then 2 ml of 50% NaOH, 0.2 ml tetrabutyl ammonium hydroxide (1.0M in MeOH), 4-fluoro-benzyl bromide (0.055 g, 0.29 mmol) are added and the reaction mixture is stirred at RT for 1.5 hours. The layers are separated and the organic solvent is removed under the reduced pressure, purified by a silica gel flash column using heptane and ethyl acetate as the elutes.

出典

DOI: 10.6084/m9.figshare.5104873.v1特許: US08536168B2uspto-grants-2013_09