Dimethyl Sulfoxide → 4-(1H-5-indolyloxy)-2-pyridinamine

HRID 1433478Notes

Reaction equation

HRID 1433478 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6](Cl)[CH:5]=[CH:4][N:3]=1.[OH:9][C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2.[H-].[Na+].CS(C)=O>O>[NH2:1][C:2]1[CH:7]=[C:6]([O:9][C:10]2[CH:11]=[C:12]3[C:16](=[CH:17][CH:18]=2)[NH:15][CH:14]=[CH:13]3)[CH:5]=[CH:4][N:3]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 160545-HydroxyindoleHCID 24758Sodium hydrideHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 219493654-(1H-5-indolyloxy)-2-pyridinamineYield 14%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Amino-4-chloropyridine (2.0 g), 5-hydroxyindole (4.1 g), sodium hydride (60% in oil, 1.25 g) and dimethylsulfoxide (20 ml) were stirred at 160° C. for 9.5 hours. Water was added, extraction was performed with ethyl acetate, and purification was performed by silica gel column chromatography (hexane:ethyl acetate=1:1, ethyl acetate). The solvent was distilled off under reduced pressure, a small amount of ethyl acetate was added to the residue and the solid was filtered out to obtain 490 mg of a light brown solid.

Workup

  1. extractionextraction
  2. customwas performed with ethyl acetate, and purification
  3. distillationThe solvent was distilled off under reduced pressure
  4. additiona small amount of ethyl acetate was added to the residue
  5. filtrationthe solid was filtered out

Sources & evidence

ORD record
ord-f69ea682fd6a445faf5225315ea5c0ad
Source dataset
uspto-grants-2009_11
Patent number
US07612092B2

Reaction notes

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