Sodium hydride → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,7-dimethyl-1H-[1,8]naphthyridin-4-one

HRID 226993Notes

Reaction equation

HRID 226993 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([CH:20]=[CH:21][C:22]=1[CH3:23])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[N:11][C:12]([CH3:19])=[C:13]([CH3:18])[CH:14]=2)[NH:9][CH:8]=1)=[O:6].[H-].[Na+].[Br:26][C:27]1[CH:32]=[CH:31][CH:30]=[C:29]([CH2:33]Br)[N:28]=1>CN(C)C=O>[Br:26][C:27]1[N:28]=[C:29]([CH2:33][N:9]2[C:10]3[C:15](=[CH:14][C:13]([CH3:18])=[C:12]([CH3:19])[N:11]=3)[C:16](=[O:17])[C:7]([C:5](=[O:6])[C:4]3[CH:20]=[CH:21][C:22]([CH3:23])=[C:2]([CH3:1])[CH:3]=3)=[CH:8]2)[CH:30]=[CH:31][CH:32]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 129547962-Bromo-6-(bromomethyl)pyridineHCID 577545333-(3,4-Dimethyl-benzoyl)-6,7-dimethyl-1H-[1,8]naphthyridin-4-one

Product 1

HCID 577547051-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,7-dimethyl-1H-[1,8]naphthyridin-4-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Experimental conditions analogous to those described for Step 2 of Example 1 were used with 69 mg (0.224 mmol) of 3-(3,4-Dimethyl-benzoyl)-6,7-dimethyl-1H-[1,8]naphthyridin-4-one, 11 mg (0.269 mmol, 60% dispersion in oil) of sodium hydride, 67.5 mg (0.269 mmol) of 2-bromo-6-bromomethyl-pyridine and 2.0 mL of N,N dimethylformamide. The crude brown solid was purified by flash column chromatography using 30-100% ethyl acetate in hexane to yield 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3,4-dimethyl-benzoyl)-6,7-dimethyl-1H-[1,8]naphthyridin-4-one as an off white solid. LC-MSD, m/z for C25H22BrN3O2 [M+H]: 476.09 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.8 min

Workup

  1. customThe crude brown solid was purified by flash column chromatography

Sources & evidence

ORD record
ord-e517e4ff2c5a418ea5583c032657538d
Source dataset
uspto-grants-2009_07
Patent number
US07557213B2

Reaction notes

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