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

HRID 227121Notes

Reaction equation

HRID 227121 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[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]=1>CN(C)C=O>[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)[N:13]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([C:32]([F:34])([F:33])[F:35])[N:27]=3)[CH:12]=2)=[O:10])[CH:5]=[N:6][C:7]=1[CH3:8]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 469414632-(Bromomethyl)-6-(trifluoromethyl)pyridineHCID 577545393-(5,6-Dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one

Product 1

HCID 577547513-(5,6-Dimethyl-pyridine-3-carbonyl)-1-(6-trifluoromethyl-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 60 mg (0.22 mmol) of 3-(5,6-dimethyl-pyridine-3-carbonyl)-1H-quinolin-4-one, 10 mg (0.26 mmol) of 60% sodium hydride, 62 mg (0.26 mmol) of 2-bromomethyl-6-trifluoromethyl-pyridine and 0.7 mL of N,N-dimethylformamide. Yield: 29 mg of a white solid: LC-MSD, m/z for C24H18F3N3O2 [M+H]+=438.1; HPLC retention time: 1.4 min.

Sources & evidence

ORD record
ord-6a4d37ee8b9a40d89aa542bf8fc2dc93
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

Loading…