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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1048874Generated: October 29, 2026

Triethylamine → 1-(4-Fluorophenyl)-4-oxo-6-vinyl-1,4-dihydroquinoline-3-carboxamide

https://huagongshe.com/reaction/1048874

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
ReactantPotassium vinyltrifluoroborateHCID 23679353—
Reactant6-Bromo-1-(4-fluorophenyl)-4-oxo-1,4-dihydroquinoline-3-carboxamideHCID 121447871—
CatalystHCID 178418807HCID 178418807—
Solvent1-PropanolHCID 1031—
Product1-(4-Fluorophenyl)-4-oxo-6-vinyl-1,4-dihydroquinoline-3-carboxamideHCID 121447866100%

Reaction Conditions

Temperature100 °C

Reaction Steps

To a solution of compound E (450 mg, 1.25 mmol), triethylamine (174 μL, 1.25 mmol), and Pd(dppf)Cl2 CH2Cl2 (18.2 mg, 0.025 mmol) in 1-propanol (8.3 mL) was added potassium vinyltrifluoroborate (200 mg, 1.50 mmol). The reaction was purged with argon and stirred at 100° C. for 16 hours. The reaction was filtered over Celite® and washed very well with a 5% MeOH in DCM solution and concentrated in vacuo to give 385 mg (100%) of the title compound that was used without further purification. ES-MS [M+1]+: 309.2.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS09382208B1
Source datasetuspto-grants-2016_07
ORD IDord-e5f840f217304ec5b7bfcd11b89d1e2c
Source noteuspto-grants-2016_07