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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 227139Generated: November 1, 2026

Sodium hydride → 6-[3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile

https://huagongshe.com/reaction/227139

Reaction equation

Participants

RoleNameHCIDCharge
ReactantSodium hydrideHCID 24758—
Reactant6-(Bromomethyl)pyridine-2-carbonitrileHCID 27281660—
Reactant3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-oneHCID 57754543—
SolventDimethylformamideHCID 6228—
Product6-[3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrileHCID 5775461117.6%

Reaction Steps

The mixture of 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one (70 mg, 0.228 mmol, 1 eq) in DMF (1 ml) and sodium hydride (11.8 mg, 0.296 mmol, 1.3 eq) was stirred at room temperature for 60 min, followed by the addition of 6-Bromomethyl-pyridine-2-carbonitrile (74.1 mg, 0.296 mmol, 1.3 eq). The mixture was stirred for 60 min, quenched with water, taken up with ethyl acetate, dried over sodium sulfate and purified with flash chromatography to give the desired product (17 mg). LCMS observed for (M+H)+: 424.1.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07557213B2
Source datasetuspto-grants-2009_07
ORD IDord-dd3947a494ca4d669105e116c3033a27
Source noteuspto-grants-2009_07