1-(6-Bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide → 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3-fluoro-4-methoxy-benzoyl)-7-trifluoromethyl-1H-[1,8]naphthyridin-4-one
Reaction equation
CON(C)[C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[N:10][C:11]([C:17]([F:20])([F:19])[F:18])=[CH:12][CH:13]=2)[N:8]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([Br:28])[N:23]=2)[CH:7]=1)=[O:5].[F:30][C:31]1[CH:32]=[C:33]([Mg]Cl)[CH:34]=[CH:35][C:36]=1[O:37][CH3:38]>C1COCC1>[Br:28][C:24]1[N:23]=[C:22]([CH2:21][N:8]2[C:9]3[C:14](=[CH:13][CH:12]=[C:11]([C:17]([F:20])([F:19])[F:18])[N:10]=3)[C:15](=[O:16])[C:6]([C:4](=[O:5])[C:33]3[CH:34]=[CH:35][C:36]([O:37][CH3:38])=[C:31]([F:30])[CH:32]=3)=[CH:7]2)[CH:27]=[CH:26][CH:25]=1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Experimental conditions analogous to those described for Step 6 of Example 60, from 80 mg of 1-(6-bromo-pyridin-2-ylmethyl)-4-oxo-7-trifluoromethyl-1,4-dihydro-[1,8]naphthyridine-3-carboxylic acid methoxy-methyl-amide, 2 mL of THF was treated with 3-fluoro-4-methoxyphenyl magnesium chloride (0.5 M in THF, 1.3 mL, 2 equiv) at rt for 2 h. The reaction was quenched by slow addition of saturated aqueous ammonium chloride. The mixture was subjected to HPLC and then preparative TLC purification to give 1-(6-Bromo-pyridin-2-ylmethyl)-3-(3-fluoro-4-methoxy-benzoyl)-7-trifluoromethyl-1H-[1,8]naphthyridin-4-one. LCMS (ES) M+H 536.0.
Workup
- customThe reaction was quenched by slow addition of saturated aqueous ammonium chloride
- custompreparative TLC purification
Sources & evidence
- ORD record
- ord-1141c0699a9746d5a576f9ee7c153f34
- Source dataset
- uspto-grants-2009_07
- Patent number
- US07557213B2
Reaction notes
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