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

HRID 227139Notes

Reaction equation

HRID 227139 reaction equation
[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[NH:15][CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1.[H-].[Na+].Br[CH2:27][C:28]1[N:33]=[C:32]([C:34]#[N:35])[CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[O:1]1[C:6]2[CH:7]=[CH:8][C:9]([C:11]([C:13]3[C:22](=[O:23])[C:21]4[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=4)[N:15]([CH2:27][C:28]4[N:33]=[C:32]([C:34]#[N:35])[CH:31]=[CH:30][CH:29]=4)[CH:14]=3)=[O:12])=[CH:10][C:5]=2[O:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 272816606-(Bromomethyl)pyridine-2-carbonitrileHCID 577545433-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577546116-[3-(2,3-Dihydro-benzo[1,4]dioxine-6-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrileYield 17.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  1. stirringThe mixture was stirred for 60 min
  2. customquenched with water
  3. dry with materialdried over sodium sulfate
  4. custompurified with flash chromatography

Sources & evidence

ORD record
ord-dd3947a494ca4d669105e116c3033a27
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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