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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1748659Generated: October 31, 2026

Ethanol → N-[6-(8-Cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-(4-fluorophenyl)nicotinamide

https://huagongshe.com/reaction/1748659

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthanolHCID 702—
ReactantSodium CarbonateHCID 10340—
Reactant4-Fluorophenylboronic acidHCID 285645—
ReactantHCID 86692599HCID 86692599—
CatalystHCID 178419050HCID 178419050—
SolventWaterHCID 962—
SolventTolueneHCID 1140—
ProductN-[6-(8-Cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]-5-(4-fluorophenyl)nicotinamideHCID 8669260015%

Reaction Conditions

Temperature100 °C

Reaction Steps

A solution of 5-bromo-N-[6-(8-cyano-1,4-dioxaspiro[4.5]dec-8-yl)pyridin-3-yl]nicotinamide (213 mg), 4-fluorophenylboronic acid (63 mg), bis(triphenylphosphine)palladium (II) dichloride (100 mg) and sodium carbonate (636 mg) in a mixture of toluene (5 ml), ethanol (1 ml) and water (1 ml) was stirred at 100° C. for six hours. After completion of the reaction, water was added and extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated. The residue was purified with column chromatography to give the titled compound (31 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09150555B2
Source datasetuspto-grants-2015_10
ORD IDord-a4c98d12a87c43ab8fc20a8df0efb0bc
Source noteuspto-grants-2015_10