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

HRID 227120Notes

Reaction equation

HRID 227120 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[CH3:21])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].[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:9]2[C:10]3[C:15](=[CH:14][CH:13]=[CH:12][CH:11]=3)[C:16](=[O:17])[C:7]([C:5](=[O:6])[C:4]3[CH:18]=[CH:19][C:20]([CH3:21])=[C:2]([CH3:1])[CH:3]=3)=[CH:8]2)[CH3:32])[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-oneHCID 577547382-Bromo-6-(1-bromoethyl)pyridine

Product 1

HCID 577546121-[1-(6-Bromo-pyridin-2-yl)-ethyl]-3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 52 mg (0.19 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 9 mg (0.23 mmol) of 60% sodium hydride, 60 mg (0.23 mmol) of 2-bromo-6-(1-bromo-ethyl)-pyridine and 0.7 mL of N,N-dimethylformamide. Yield: 32 mg of a white solid: LC-MSD, m/z for C25H21BrN2O2 [M+H]+=461.0, 463.0; HPLC retention time: 2.6 min.

Sources & evidence

ORD record
ord-2e2ac84c742047ec9c67c2dd914293f2
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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