Back
HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1429944Generated: October 31, 2026

Hydrochloric Acid → 3-(2,3-dihydro-1H-indol-5-yl)-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-one

https://huagongshe.com/reaction/1429944

Reaction equation

Participants

RoleNameHCIDCharge
ReactantHydrochloric AcidHCID 313—
Reactanttert-Butyl 5-[1-(1-methylethyl)-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylateHCID 58577369—
SolventEthyl AcetateHCID 8857—
SolventTetrahydrofuran ethyl acetateHCID 21939870—
Product3-(2,3-dihydro-1H-indol-5-yl)-1-(1-methylethyl)-1,3-dihydro-2H-imidazo[4,5-b]pyridin-2-oneHCID 58577255—

Reaction Conditions

Temperature80 °C

Reaction Steps

To a stirred mixture of tert-butyl 5-[1-(1-methylethyl)-2-oxo-1,2-dihydro-3H-imidazo[4,5-b]pyridin-3-yl]-2,3-dihydro-1H-indole-1-carboxylate in AcOEt/EtOH (1/1, 10 mL) was added 4N HCl in AcOEt (4 mL). The mixture was stirred at 80° C. for 2 h, evaporated, treated with saturated NaHCO3, and extracted with AcOEt. The organic layer was dried over MgSO4 and concentrated in vacuo. The residue was suspended in IPE and the suspension was collected by filtration to give the title compound as white crystals (313 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08940758B2
Source datasetuspto-grants-2015_01
ORD IDord-4fdf5a7071bc4bdcb0cfff44a6c41d3b
Source noteuspto-grants-2015_01