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

HRID 387826Notes

Reaction equation

HRID 387826 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-8192182d29894dd7b4ea7dedfdf79f21
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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