Dimethylformamide → 3-(3-Fluoro-4-methoxy-benzoyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-quinolin-4-one
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[NH:9][CH:8]=1)=[O:6].Br[CH2:24][C:25]1[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[N:26]=1.CN(C)C=O>O>[F:1][C:2]1[CH:3]=[C:4]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:5]([C:7]1[C:16](=[O:17])[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[N:9]([CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:33])([F:32])[F:34])[N:26]=2)[CH:8]=1)=[O:6]Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Procedure
Experimental conditions analogous to those described for Step 3 of Example 1 were used with 150 mg (0.505 mmol) of 3-(3-Fluoro-4-methoxy-benzoyl)-1H-quinolin-4-one, 145.3 mg (0.605 mmol) of 2-bromomethyl-6-trifluoromethyl-pyridine, 24.2 mg (0.605 mmol, 60% dispersion in oil), and 1 mL of N,N dimethylformamide. Water was added and the solid was collected by filtration. The crude product was purified by flash column chromatography using a gradient of 20-100% ethyl acetate in hexane to yield 195.9 mg of 3-(3-Fluoro-4-methoxy-benzoyl)-1-(6-trifluoromethyl-pyridin-2-ylmethyl)-1H-quinolin-4-one. LC-MSD, m/z for C24H16F4N2O3 [M+H]: 457.11 LC retention time on HPLC, C18 column gradient 20-95% acetonitrile with 0.1% TFA in 4 minutes: 2.5 min.
Workup
- filtrationthe solid was collected by filtration
- customThe crude product was purified by flash column chromatography
Sources & evidence
- ORD record
- ord-0a7db37ff49b49f190c11aabfcaf708c
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557213B2
Reaction notes
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