HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium hydride → 6-[3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium hydride | HCID 24758 | — |
| Reactant | 6-(Bromomethyl)pyridine-2-carbonitrile | HCID 27281660 | — |
| Reactant | 3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one | HCID 57754543 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | 6-[3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile | HCID 57754611 | 17.6% |
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
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07557213B2 |
| Source dataset | uspto-grants-2009_07 |
| ORD ID | ord-dd3947a494ca4d669105e116c3033a27 |
| Source note | uspto-grants-2009_07 |