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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 853349Generated: October 29, 2026

Water → N1-cyclopropyl-5-((2-amino-4-pyridyl)oxy)-1H-1-indolecarboxamide

https://huagongshe.com/reaction/853349

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
ReactantPhenyl cyclopropylcarbamateHCID 13648483—
Reactant4-(1H-5-indolyloxy)-2-pyridinamineHCID 21949365—
SolventDimethylformamideHCID 6228—
ProductN1-cyclopropyl-5-((2-amino-4-pyridyl)oxy)-1H-1-indolecarboxamideHCID 219492361,168.8%

Reaction Conditions

Temperature0 °C

Reaction Steps

After adding 28 mg of sodium hydride (60% in oil) to a solution of 150 mg of 5-[(2-amino-4-pyridyl)oxy]-1H-indole in dimethylformamide at room temperature and stirring for 5 minutes, the mixture was cooled to 0° C., 124 mg of phenyl N-cyclopropylcarbamate was added and the mixture was further stirred for 30 minutes. Water was added, extraction was performed with ethyl acetate, the organic layer was washed 3 times with water and once with aqueous ammonium chloride solution, and then silica gel was added and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel and purification was performed by column chromatography (hexane:ethyl acetate=1:1, followed by ethyl acetate), to obtain 2.4 g of a colorless powder.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07253286B2
Source datasetuspto-grants-2007_08
ORD IDord-e94aea7dbefa4f069b06a129654f4e39
Source noteuspto-grants-2007_08