3-Bromobenzyl bromide → 1-(3-Bromo-benzyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one
Reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH3:20])[N:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:23].[Br:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([CH2:31]Br)[CH:26]=1>CN(C)C=O>[Br:24][C:25]1[CH:26]=[C:27]([CH:28]=[CH:29][CH:30]=1)[CH2:31][N:11]1[C:12]2[C:17](=[N:16][C:15]([CH3:20])=[CH:14][CH:13]=2)[C:18](=[O:19])[C:9]([C:7](=[O:8])[C:6]2[CH:21]=[CH:22][C:3]([O:2][CH3:1])=[C:4]([CH3:23])[CH:5]=2)=[CH:10]1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Experimental conditions analogous to those described for Step 3 of Example 1 were used with 120 mg (0.390 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one, 116.8 mg (0.467 mmol) of 1-bromo-3-bromomethyl-benzene, 19 mg (0.467 mmol, 60% dispersion in oil), and 1 mL of N,N dimethylformamide. The crude product was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane and further purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA to yield 36.6 mg of 1-(3-Bromo-benzyl)-3-(4-methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C25H21BrN2O3 [M+H]: 477.07 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.4 min.
Workup
- customThe crude product was purified by flash column chromatography
- customfurther purified on the reverse phase HPLC with a C18 column, gradient of 20-70% acetonitrile—0.1% TFA
Sources & evidence
- ORD record
- ord-c109d26cad28423eb007b97e7c198834
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557213B2
Reaction notes
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