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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1811262Generated: November 1, 2026

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

https://huagongshe.com/reaction/1811262

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 numberUS08362251B2
Source datasetuspto-grants-2013_01
ORD IDord-f771d17ca4cf440f80cf61bae4b32dc1
Source noteuspto-grants-2013_01