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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1983652Generated: October 26, 2026

Ethanol → 4-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-ethoxycarbonyl-[1]benzoxepino[2,3-b]pyridin-5-ylidene) propyl]piperidine-4-ol

https://huagongshe.com/reaction/1983652

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantDimethylformamideHCID 6228—
ReactantTriethylamineHCID 8471—
Reactant1,3-Bis(diphenylphosphino)propaneHCID 81219—
Reactant4-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-trifluoromethanesulfonyloxy[1]benzoxepino[2,3-b]pyridin-5-ylidene)propyl]piperidin-4-olHCID 73455970—
Catalystpalladium(II) acetateHCID 167845—
Product4-(4-Chlorophenyl)-1-[3-(5,11-dihydro-7-ethoxycarbonyl-[1]benzoxepino[2,3-b]pyridin-5-ylidene) propyl]piperidine-4-olHCID 6675868373%

Reaction Conditions

Temperature60 °C

Reaction Steps

The compound of Example 169 (0.166 g) was dissolved in DMF (1 ml) and treated with palladium (II) acetate (0.007 g), 1,3-bis-diphenylphosphinopropane (0.012 g), triethylamine (0.1 ml) and ethanol (1 ml), and stirred at 60° C. for 18 hours under a CO balloon. The resulting solution was quenched with water, extracted with ethyl acetate, concentrated in vacuo, and purified by silica gel chromatography (87:10:3 ethyl acetate:methanol:triethylamine). The residue was further purified by chromatography on a reverse-phase solid-phase-extraction column, eluting with water-acetonitrile, 0.1% formic acid, to yield 0.114 g (73%) of the title compound.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07541365B2
Source datasetuspto-grants-2009_06
ORD IDord-f6995df9dfa144c79a9072e3c83514c2
Source noteuspto-grants-2009_06