Dimethyl Sulfoxide → 4-(3-Methyl-1H-5-indolyl)oxy-2-pyridinamine

HRID 2376887Notes

Reaction equation

HRID 2376887 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH3:11].[NH2:12][C:13]1[CH:18]=[C:17](Cl)[CH:16]=[CH:15][N:14]=1.[H-].[Na+].CS(C)=O>O>[CH3:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([O:1][C:17]3[CH:16]=[CH:15][N:14]=[C:13]([NH2:12])[CH:18]=3)[CH:3]=2)[NH:7][CH:6]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 24758Sodium hydrideHCID 1927343-methyl-1H-indol-5-olHCID 5818662-Amino-4-chloropyridine

Product 1

HCID 219492824-(3-Methyl-1H-5-indolyl)oxy-2-pyridinamineYield 21%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 5-hydroxy-3-methylindole (4.7 g), 2-amino-4-chloropyridine (4.1 g), sodium hydride (1.3 g), and dimethyl sulfoxide (40 ml) was stirred at 160° C. for 15 hours. Water was added thereto; extraction was performed with ethyl acetate; and purification was performed by silica gel column chromatography (ethyl acetate, sequentially, ethyl acetate:methanol=20:1). The solvent was distilled off to yield the title compound as a brown solid (1.6 g).

Workup

  1. extractionextraction
  2. customand purification
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-78995b65703740a5af748259a5a9f5c7
Source dataset
uspto-grants-2008_12
Patent number
US07468380B2

Reaction notes

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