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

HRID 227110Notes

Reaction equation

HRID 227110 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].Br.Br[CH2:30][C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=1>CN(C)C=O>[CH3:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[CH3:25])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:18]([F:21])([F:19])[F:20])[CH:14]=2)[N:9]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][N:32]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27347202-(Bromomethyl)pyridine hydrobromideHCID 577545723-(3,4-dimethyl-benzoyl)-6-trifluoromethyl-1H-quinolin-4-one

Product 1

HCID 167306163-(3,4-Dimethyl-benzoyl)-1-pyridin-2-ylmethyl-6-trifluoromethyl-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 (0.16 mmol) of 3-(3,4-dimethyl-benzoyl)-6-trifluoromethyl-1H-quinolin-4-one, 18 mg of 60% sodium hydride, 52 mg of 2-bromomethylpyridine hydrobromide and 1 mL of N,N-dimethylformamide. Yield: 49 mg of a white solid: LC-MSD, m/z for C25H19F2N2O2 [M+H]+=437.5; HPLC retention time: 2.6 min.

Sources & evidence

ORD record
ord-048680068a6947d9bd1054f4e7a147b8
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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