Cesium carbonate → Methyl 2-methyl-1-{[3-(methyloxy)phenyl]methyl}-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylate

HRID 734760Notes

Reaction equation

HRID 734760 reaction equation
[F:1][C:2]([F:22])([F:21])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][C:13](=[O:15])[NH:12][C:11]([CH3:16])=[C:10]2[C:17]([O:19][CH3:20])=[O:18])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH3:29][O:30][C:31]1[CH:32]=[C:33]([CH:36]=[CH:37][CH:38]=1)[CH2:34]Br>CN(C=O)C.O>[CH3:16][C:11]1[N:12]([CH2:34][C:33]2[CH:36]=[CH:37][CH:38]=[C:31]([O:30][CH3:29])[CH:32]=2)[C:13](=[O:15])[CH2:14][CH:9]([C:6]2[CH:5]=[CH:4][C:3]([C:2]([F:21])([F:1])[F:22])=[CH:8][CH:7]=2)[C:10]=1[C:17]([O:19][CH3:20])=[O:18]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2854419HCID 2854419, compoundHCID 40672073-Methoxybenzyl bromide

Product 1

HCID 68828345Methyl 2-methyl-1-{[3-(methyloxy)phenyl]methyl}-6-oxo-4-[4-(trifluoromethyl)phenyl]-1,4,5,6-tetrahydro-3-pyridinecarboxylateYield 88%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

The product from Example 5, Step 1 (0.627 g, 2.00 mmol, 1.00 equiv) and cesium carbonate (0.975 g, 3.00 mmol, 1.50 equiv) were combined in DMF (9 mL) for 15 minutes at rt. 3-Methoxybenzyl bromide (0.436 mL, 3.12 mmol, 1.56 equiv) was added and the reaction was heated to 100° C. for 6 hours. The reaction was diluted with H2O and extracted with Et2O. The organic phase was washed with H2O and satd. NaCl, dried over MgSO4 and concentrated en vacuo to provide 0.762 mg (88%) of the title compound as an oil. MS (ES+) m/e 434 [M+H]+

Workup

  1. extractionextracted with Et2O
  2. washThe organic phase was washed with H2O and satd
  3. dry with materialNaCl, dried over MgSO4
  4. concentrationconcentrated en vacuo

Sources & evidence

ORD record
ord-42d6c4c192cd46508837318600254ffc
Source dataset
uspto-grants-2009_09
Patent number
US07592357B2

Reaction notes

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