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-(4-methoxy-3-methyl-benzoyl)-1H-[1,8]naphthyridin-4-one

HRID 227145Notes

Reaction equation

HRID 227145 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:33]=[CH:32][C:31]([Mg]Cl)=[CH:30][C:29]=1[CH3:36]>>[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:32]=[CH:33][C:28]([O:27][CH3:26])=[C:29]([CH3:36])[CH:30]=3)=[CH:7]2)[CH:23]=[CH:22][CH:21]=1

Participants

3

Reactant 2

HCID 577545871-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amideHCID 178491925HCID 178491925, compound

Product 1

HCID 577546941-(6-Bromo-pyridin-2-ylmethyl)-3-(4-methoxy-3-methyl-benzoyl)-1H-[1,8]naphthyridin-4-one

Procedure

Experimental conditions analogous to those described for Step 6 of Example 60, from 55 mg (0.136 mmol) of 1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide, and 0.5 ml (0.285 mmol) of 4-methoxy-3-methylphenyl magnesium chloride, to give desired compound as a white solid. LCMS (M+H)+: 464.

Sources & evidence

ORD record
ord-535674a3cecb49b8809f8038df777032
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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