Sodium hydride → 3-(5,6-Dimethyl-pyridine-2-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 227117Notes

Reaction equation

HRID 227117 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[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N: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[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)[CH:12]=2)=[O:10])=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 125437332-(Bromomethyl)-6-methylpyridineHCID 577545223-(5,6-Dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577546783-(5,6-Dimethyl-pyridine-2-carbonyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 95 mg (0.34 mmol) of 3-(5,6-dimethyl-pyridine-2-carbonyl)-1H-quinolin-4-one, 16 mg (0.41 mmol) of 60% sodium hydride, 77 mg (0.41 mmol) of 2-bromomethyl-6-methyl-pyridine and 1 mL of N,N-dimethylformamide. Yield: 14 mg of a white solid: LC-MSD, m/z for C24H21N3O2 [M+H]+=384.1; HPLC retention time: 1.9 min.

Sources & evidence

ORD record
ord-bf888902b4354385b201fdd94ef92176
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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