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

HRID 227113Notes

Reaction equation

HRID 227113 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[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N: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[CH:31]=[CH:30][CH:29]=[C:28]([F:32])[N:27]=2)[CH:8]=1)=[O:6]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139852182-(Bromomethyl)-6-fluoropyridineHCID 577545153-(3,4-Dimethyl-benzoyl)-1H-quinolin-4-one

Product 1

HCID 577546823-(3,4-Dimethyl-benzoyl)-1-(6-fluoro-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 49 mg (0.18 mmol) of 3-(3,4-dimethyl-benzoyl)-1H-quinolin-4-one, 8 mg (0.21 mmol) of 60% sodium hydride, 40 mg (0.21 mmol) 2-bromomethyl-6-fluoro-pyridine and 0.8 mL of N,N-dimethylformamide. Yield: 28 mg of a white solid: LC-MSD, m/z for C24H19FN2O2 [M+H]+=387.3; HPLC retention time: 2.6 min.

Sources & evidence

ORD record
ord-6ca77adc091b4bcfb6ae347d6fc1ce00
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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