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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

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantEthyl AcetateHCID 8857—
ReactantSodium MethoxideHCID 10942334—
ReactantN-(4-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamideHCID 86730322—
SolventMethanolHCID 887—
Product4-((6-Isopropoxy-1H-indol-5-yl)oxy)pyridin-2-amineHCID 8673032466%

Reaction Conditions

Temperature70 °C

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

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08933099B2
Source datasetuspto-grants-2015_01
ORD IDord-7351a794a4af424abfa4222e96c151a8
Source noteuspto-grants-2015_01