2-(Bromomethyl)-6-methylpyridine → 6,7-Dimethyl-1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

HRID 226996Notes

Reaction equation

HRID 226996 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([CH3:18])=[C:12]([CH3:17])[CH:13]=2)[NH:8][CH:7]=1)=[O:5])[CH3:2].Br[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=1>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([CH3:18])=[C:12]([CH3:17])[CH:13]=2)[N:8]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[N:22]=2)[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 125437332-(Bromomethyl)-6-methylpyridineHCID 577545266,7-Dimethyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester

Product 1

HCID 577547046,7-Dimethyl-1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl esterYield 37.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 3 of Example 60 were used with 3 g (12.17 mmol) of 6,7-Dimethyl-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester, 2.49 g (13.39 mmol) of 2-Bromomethyl-6-methyl-pyridine, 0.54 g (13.39 mmol, 60% dispersion in oil), and 60 mL of N,N-dimethylformamide to give 1.61 g of 6,7-Dimethyl-1-(6-methyl-pyridin-2-ylmethyl)-4-oxo-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid ethyl ester.

Sources & evidence

ORD record
ord-d3404971b1d24280a356eeffec04e655
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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