1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethoxy-benzoyl)-1H-[1,8]naphthyridin-4-one

HRID 227133Notes

Reaction equation

HRID 227133 reaction equation
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][CH:11]=[CH:12][CH:13]=2)[N:8]([CH2:17][C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([Br:24])[N:19]=2)[CH:7]=1)=[O:5].[CH3:26][O:27][C:28]1[CH:29]=[C:30]([Mg]Br)[CH:31]=[CH:32][C:33]=1[O:34][CH3:35]>C1COCC1>[Br:24][C:20]1[N:19]=[C:18]([CH2:17][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][N:10]=3)[C:15](=[O:16])[C:6]([C:4](=[O:5])[C:31]3[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[C:33]([O:34][CH3:35])[CH:32]=3)=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 577545871-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amideHCID 178491916HCID 178491916, compound

Product 1

HCID 577546341-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethoxy-benzoyl)-1H-[1,8]naphthyridin-4-oneYield 18.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 100 mg (0.248 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide in THF 2 ml, was added 1.09 ml (0.545 mmol) 3,4-dimethoxyphenylmagnesium bromide. The reaction mixture was stirred at room temperature for 30 min, then quenched with saturated solution of NH4Cl, extracted with ethyl acetate and purified with flash chromatography to give the desired product 22 mg. LCMS observed for (M+H)+: 480.

Workup

  1. customquenched with saturated solution of NH4Cl
  2. extractionextracted with ethyl acetate
  3. custompurified with flash chromatography

Sources & evidence

ORD record
ord-ff776be363784da2a99a419d704eaf53
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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