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
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethyl Sulfoxide | HCID 679 | — |
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 3-methyl-1H-indol-5-ol | HCID 192734 | — |
| Reactant | 2-Amino-4-chloropyridine | HCID 581866 | — |
| Solvent | Water | HCID 962 | — |
| Product | 4-(3-Methyl-1H-5-indolyl)oxy-2-pyridinamine | HCID 21949282 | 21% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07468380B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-78995b65703740a5af748259a5a9f5c7 |
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| Source note | uspto-grants-2008_12 |
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