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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2376887Generated: October 30, 2026

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

https://huagongshe.com/reaction/2376887

Reaction equation

Participants

RoleNameHCIDCharge
ReactantDimethyl SulfoxideHCID 679—
ReactantSodium hydrideHCID 24758—
Reactant3-methyl-1H-indol-5-olHCID 192734—
Reactant2-Amino-4-chloropyridineHCID 581866—
SolventWaterHCID 962—
Product4-(3-Methyl-1H-5-indolyl)oxy-2-pyridinamineHCID 2194928221%

Reaction Conditions

Temperature160 °C

Reaction Steps

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).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07468380B2
Source datasetuspto-grants-2008_12
ORD IDord-78995b65703740a5af748259a5a9f5c7
Source noteuspto-grants-2008_12