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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2365060Generated: November 1, 2026

Piperidine → N-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-methoxyacetamide

https://huagongshe.com/reaction/2365060

Reaction equation

Participants

RoleNameHCIDCharge
ReactantPiperidineHCID 8082—
ReactantMethoxyacetyl chlorideHCID 96623—
Reactant2-(6-Amino-5-fluoro-2-oxo-1,2-dihydro-indol-3-ylidenemethyl)-5-(2-diethylamino-ethyl)-3-methyl-1,5,6,7-tetrahydro-pyrrolo[3,2-c]pyridin-4-oneHCID 66607288—
SolventTetrahydrofuranHCID 8028—
ProductN-(5-Fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-methoxyacetamideHCID 4511814869.2%

Reaction Conditions

Temperature-50 °C

Reaction Steps

A stirred solution of d 6-amino-5-fluoro-1,3-dihydro-indol-2-one (2.028 g, 12.2 mmol) obtained from Example 7 in 30 ml of tetrahydrofuran was added with piperidine (1.3 ml). The mixture was cooled to −50° C. in an ethanol-dry ice bath and added with methoxyacetyl chloride (1.35 g, 12.5 mmol) in 20 ml of tetrahydrofuran dropwise. Upon the completion of the addition, the resulting mixture was stirred at the room temperature overnight until the precipitate was formed. The solid was filtered, washed with water and recrystallized from methanol to give N-(5-fluoro-2-oxo-2,3-dihydro-1H-indol-6-yl)-2-methoxy-acetamide (2.0 g, 69.2%) as a white solid.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08697692B2
Source datasetuspto-grants-2014_04
ORD IDord-220aabd5860d4a849455994923277d0c
Source noteuspto-grants-2014_04