4-glycidyloxy-2-indolecarbonitrile → HCID 14405372, compound

HRID 2107526Notes

Reaction equation

HRID 2107526 reaction equation
[O:1]1[CH2:16][CH:2]1[CH2:3][O:4][C:5]1[CH:13]=[CH:12][CH:11]=[C:10]2[C:6]=1[CH:7]=[C:8]([C:14]#[N:15])[NH:9]2.[F:17][CH:18]([F:39])[O:19][C:20]1[CH:25]=[CH:24][C:23]([CH:26]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:27]2[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]2)=[CH:22][CH:21]=1>CO>[F:39][CH:18]([F:17])[O:19][C:20]1[CH:21]=[CH:22][C:23]([CH:26]([C:33]2[CH:34]=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:27]2[CH2:32][CH2:31][N:30]([CH2:16][CH:2]([OH:1])[CH2:3][O:4][C:5]3[CH:13]=[CH:12][CH:11]=[C:10]4[C:6]=3[CH:7]=[C:8]([C:14]#[N:15])[NH:9]4)[CH2:29][CH2:28]2)=[CH:24][CH:25]=1

Participants

4

Reactant 2

HCID 117905614-glycidyloxy-2-indolecarbonitrileHCID 14405370HCID 14405370, compound

Product 1

HCID 14405372HCID 14405372, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2.5 g of 4-(2,3-epoxypropoxy)-1H-indole-2-carbonitrile and 3.7 g of 1-((4-difluoromethoxyphenyl)phenylmethyl)piperazine are dissolved in 50 ml of methanol and heated for 3 hours under reflux. The mixture is then concentrated to dryness in vacuo and the residue is triturated with hexane, filtered off with suction and purified by column chromatography on silica gel (eluent: chloroform/methanol 40:2).

Workup

  1. temperatureheated for 3 hours
  2. temperatureunder reflux
  3. concentrationThe mixture is then concentrated to dryness in vacuo
  4. customthe residue is triturated with hexane
  5. filtrationfiltered off with suction
  6. custompurified by column chromatography on silica gel (eluent: chloroform/methanol 40:2)

Sources & evidence

ORD record
ord-776536ea11424db09545292c1478f62f
Source dataset
uspto-grants-1990_06
Patent number
US04935414

Reaction notes

Loading…