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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1437155Generated: October 27, 2026

Water → 4-[1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid ethyl ester

https://huagongshe.com/reaction/1437155

Reaction equation

Participants

RoleNameHCIDCharge
ReactantWaterHCID 962—
ReactantSodium hydrideHCID 24758—
Reactant2-Bromoethyl methyl etherHCID 80972—
ReactantEthyl 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylateHCID 49759051—
SolventDimethylformamideHCID 6228—
Product4-[1-(2-methoxyethyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-piperidine-1-carboxylic acid ethyl esterHCID 68894419—

Reaction Steps

1.0 g (3.66 mmol) of 4-(1H-pyrrolo[2,3-b]pyridin-3-yl)piperidine-1-carboxylic acid ethyl ester were dissolved in 10 ml of DMF and, at room temperature, 0.19 g (4.76 mmol) of 60% sodium hydride were carefully added. This mixture was stirred for half an hour. 0.45 ml (5.12 mmol) of 1-bromo-2-methoxyethane were added dropwise and the mixture was further stirred for 24 hours at 60° C. The reaction mixture was cooled to room temperature and poured over cold water. The aqueous phase was extracted twice with dichloromethane and the organic phase was washed with water and brine, dried with magnesium sulphate, filtered and evaporated to dryness. This resulted in 0.86 g (71% of yield) of product.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07622480B2
Source datasetuspto-grants-2009_11
ORD IDord-3e6d48007ffa4e75a7b0bd55a6579385
Source noteuspto-grants-2009_11