HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1427021Generated: October 27, 2026
Water → 4-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-amine
https://huagongshe.com/reaction/1427021
Participants
| Role | Name | HCID | Charge |
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| Reactant | Water | HCID 962 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | Sodium Methoxide | HCID 10942334 | — |
| Reactant | N-(4-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide | HCID 86730322 | — |
| Solvent | Methanol | HCID 887 | — |
| Product | 4-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-amine | HCID 86730324 | 66% |
Reaction Steps
N-(4-((6-isopropoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 17-5 (116 mg, 0.357 mmol) was dissolved in methanol (2.5 mL), 28% sodium methoxide (0.728 mL) was added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 70° C. for 3 hours. The reaction mixture was cooled to room temperature and then water and ethyl acetate were added for partition. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was filtered off and the resultant was concentrated under vacuum. The residue was dissolved in dichloromethane and the resultant was purified with silica gel column chromatography (n-heptane:ethyl acetate=3:7-0:1-ethyl acetate:methanol=99:1-9:1), then the target fraction was concentrated under vacuum to obtain the title compound (66.3 mg, 66%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08933099B2 |
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| Source dataset | uspto-grants-2015_01 |
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| ORD ID | ord-7351a794a4af424abfa4222e96c151a8 |
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| Source note | uspto-grants-2015_01 |
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