Sodium hydride → 6-[3-(5,6-Dimethyl-pyridine-2-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile

HRID 227123Notes

Reaction equation

HRID 227123 reaction equation
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[NH:13][CH:12]=2)=[O:10])=[N:6][C:7]=1[CH3:8].[H-].[Na+].Br[CH2:25][C:26]1[N:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][CH:27]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]([C:11]2[C:20](=[O:21])[C:19]3[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:25][C:26]3[N:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][CH:27]=3)[CH:12]=2)=[O:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 272816606-(Bromomethyl)pyridine-2-carbonitrileHCID 577545223-(5,6-Dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577545866-[3-(5,6-Dimethyl-pyridine-2-carbonyl)-4-oxo-4H-quinolin-1-ylmethyl]-pyridine-2-carbonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 67 mg (0.24 mmol) of 3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one, 12 mg (0.29 mmol) of 60% sodium hydride, 57 mg (0.29 mmol) of 6-bromomethyl-pyridine-2-carbonitrile and 0.7 mL of N,N-dimethylformamide. Yield: 34 mg of a white solid: LC-MSD, m/z for C24H18N4O2 [M+H]+=395.1; HPLC retention time: 1.0 min.

Sources & evidence

ORD record
ord-bb08d8e3beab4c4a8b5332a5578eb88b
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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