Sodium hydride → 1-[1-(6-Bromo-pyridin-2-yl)-ethyl]-3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

HRID 227118Notes

Reaction equation

HRID 227118 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([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])[CH:5]=[N:6][C:7]=1[CH3:8].[H-].[Na+].[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH:31](Br)[CH3:32])[N:26]=1>CN(C)C=O>[Br:24][C:25]1[N:26]=[C:27]([CH:31]([N:13]2[C:14]3[C:19](=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:20](=[O:21])[C:11]([C:9]([C:4]3[CH:5]=[N:6][C:7]([CH3:8])=[C:2]([CH3:1])[CH:3]=3)=[O:10])=[CH:12]2)[CH3:32])[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 577545393-(5,6-Dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-oneHCID 577547382-Bromo-6-(1-bromoethyl)pyridine

Product 1

HCID 577545501-[1-(6-Bromo-pyridin-2-yl)-ethyl]-3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 55 mg (0.20 mmol) of 3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one, 10 mg (0.26 mmol) of 60% sodium hydride, 68 mg (0.26 mmol) of 2-bromo-6-(1-bromo-ethyl)-pyridine and 0.7 mL of N,N-dimethylformamide. Yield: 24 mg of a white solid: LC-MSD, m/z for C24H20BrN3O2 [M+H]+=462.0, 464.0; HPLC retention time: 1.4 min.

Sources & evidence

ORD record
ord-42cf855bc93a4dab8d460ad92579c008
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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