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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 533150Generated: October 29, 2026

Cesium carbonate → 6-(4-methoxybenzyl)-2-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-one

https://huagongshe.com/reaction/533150

Reaction equation

Participants

RoleNameHCIDCharge
ReactantCesium carbonateHCID 10796—
ReactantPotassium vinyltrifluoroborateHCID 23679353—
Reactant2-chloro-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-oneHCID 86667502—
CatalystHCID 178418397HCID 178418397—
SolventEthanolHCID 702—
Product6-(4-methoxybenzyl)-2-vinyl-7,8-dihydro-1,6-naphthyridin-5(6H)-oneHCID 68008022—

Reaction Conditions

Temperature150 °C

Reaction Steps

2-chloro-6-(4-methoxybenzyl)-7,8-dihydro-1,6-naphthyridin-5(6H)-one, (1.5 g, 4.97 mmol) was dissolved in EtOH with potassium vinyltrifluoroborate (865 mg, 6.46 mmol), Cs2CO3 (2.42 g, 7.46 mmol) and Pd(PPh3)4 (115 mg, 0.01 mmol). The reaction was heated in a microwave synthesizer at 150° C. for 1 h. It was then concentrated and purified over silica gel (EtOAc/hexanes) to give after solvent removal and drying in vacuo the compound as an off-white solid (1.1 g, 76%). LC-MS (M+H)=295.2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08853237B2
Source datasetuspto-grants-2014_10
ORD IDord-342ee0c5ba904e8880c8d1039abbf66f
Source noteuspto-grants-2014_10