1-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amide → 3-(3-Fluoro-4-methoxy-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

HRID 227076Notes

Reaction equation

HRID 227076 reaction equation
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[CH:7]=1)=[O:5].[F:26][C:27]1[CH:28]=[C:29]([Mg]Br)[CH:30]=[CH:31][C:32]=1[O:33][CH3:34]>C1COCC1>[F:26][C:27]1[CH:28]=[C:29]([CH:30]=[CH:31][C:32]=1[O:33][CH3:34])[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[N:19]=2)[CH:7]=1)=[O:5]

Participants

4

Reactant 2

HCID 577545121-(6-Methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl amideHCID 178491915HCID 178491915, compound

Product 1

HCID 577546633-(3-Fluoro-4-methoxy-benzoyl)-1-(6-methyl-pyridin-2-ylmethyl)-1H-quinolin-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 120 mg (0.36 mmol) of 1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid methoxy-methyl-amide in 2 mL THF and 1.6 mL 0.5M 3-fluoro-4-methoxyphenylmagnesium bromide. Yield: 95 mg of a white solid. LC-MSD, m/z for C24H19FN2O3 [M+H]+=403.1; HPLC retention time: 1.9 min.

Sources & evidence

ORD record
ord-500b8eddd791411c805a186c1d77add3
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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