2-(Bromomethyl)-6-methylpyridine → 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1-(6-methyl-pyridin-2-ylmethyl)-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[CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=1>CN(C)C=O>[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)[N:11]([CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[C:28]([CH3:32])[N:27]=3)[CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:23]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Experimental conditions analogous to those described for Step 3 of Example 1 were used with 100 mg (0.324 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1H-[1,5]naphthyridin-4-one, 72.4 mg (0.389 mmol) of 2-Bromomethyl-6-methyl-pyridine, 15.6 mg (0.389 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 34.8 mg of 3-(4-Methoxy-3-methyl-benzoyl)-6-methyl-1-(6-methyl-pyridin-2-ylmethyl)-1H-[1,5]naphthyridin-4-one. LC-MSD, m/z for C25H23N3O3 [M+H]: 414.17 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 1.8 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-2b7b390f6205456a84852a1a209b82dd
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557213B2
Reaction notes
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