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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2205963Generated: October 23, 2026

Water → 3-bromo-1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one

https://huagongshe.com/en/reaction/2205963

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
Reactanttrimethylsilyl N-trimethylsilylethanimidateHCID 25248—
ReactantN-bromobutanimideHCID 67184—
Reactant1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-oneHCID 117987824—
SolventDimethylformamideHCID 6228—
Product3-bromo-1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-oneHCID 11798849369.4%

Reaction Conditions

Temperature40 °C

Reaction Steps

To a solution of 1-cyclopentyl-1,5-dihydro-4H-pyrrolo[3,2-c]pyridin-4-one (3.40 g) in DMF (42.0 mL) was added trimethylsilyl N-(trimethylsilyl)ethanimidate (7.52 g) at room temperature, and the mixture was stirred at 40° C. for 3 hr. The reaction mixture was allowed to be cooled to room temperature, and NBS (3.59 g) was added thereto at room temperature. The reaction mixture was stirred overnight at room temperature, water was added thereto, and the mixture was stirred at room temperature for 2 hr. The white precipitate was collected by filtration, and dried under reduced pressure to give the title compound (3.28 g).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09371320B2
Source datasetuspto-grants-2016_06
ORD IDord-f96fa7a44c5d4f9cb7b5f2f9ff9ae4cd
Source noteuspto-grants-2016_06