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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 387827Generated: October 27, 2026

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

https://huagongshe.com/reaction/387827

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 ammonium chloride water, 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 numberUS08372981B2
Source datasetuspto-grants-2013_02
ORD IDord-64f1e599f0124527aebf5fd2afb0f077
Source noteuspto-grants-2013_02