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

HRID 227124Notes

Reaction equation

HRID 227124 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[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]=[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)[N:9]([CH2:25][C:26]2[N:31]=[C:30]([C:32]#[N:33])[CH:29]=[CH:28][CH:27]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 272816606-(Bromomethyl)pyridine-2-carbonitrileHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 167312506-[3-(3,4-Dimethyl-benzoyl)-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 51 mg (0.18 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 9 mg (0.22 mmol) of 60% sodium hydride, 44 mg (0.22 mmol) of 6-bromomethyl-pyridine-2-carbonitrile and 0.7 mL of N,N-dimethylformamide. Yield: 27 mg of a white solid: LC-MSD, m/z for C25H19N3O2 [M+H]+=394.1; HPLC retention time: 2.1 min.

Sources & evidence

ORD record
ord-cbf8e5ad37ab4762b98ea835ecfce75e
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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