Cesium carbonate → HCID 57595388, compound

HRID 1785994Notes

Reaction equation

HRID 1785994 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C@H:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[N:15]([C:22](=[O:32])[C:23]3[CH:28]=[C:27]([F:29])[C:26]([OH:30])=[C:25]([F:31])[CH:24]=3)[C@@H:14]([CH3:33])[CH2:13]2)[C:9](=[O:11])[CH3:10])=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].Br[CH2:41][CH2:42][C:43]([CH3:49])([CH3:48])[C:44]([O:46][CH3:47])=[O:45]>CN(C=O)C>[C:9]([N:8]([C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)[C@H:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:15]([C:22]([C:23]2[CH:28]=[C:27]([F:29])[C:26]([O:30][CH2:41][CH2:42][C:43]([CH3:49])([CH3:48])[C:44]([O:46][CH3:47])=[O:45])=[C:25]([F:31])[CH:24]=2)=[O:32])[C@@H:14]([CH3:33])[CH2:13]1)(=[O:11])[CH3:10]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11705499HCID 11705499, compoundHCID 14928877Butanoic acid, 4-bromo-2,2-dimethyl-, methyl ester

Product 1

HCID 57595388HCID 57595388, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(4-chlorophenyl)-N-[(2S,4R)-1-(3,5-difluoro-4-hydroxybenzoyl)-2-methyl-1,2,3,4-tetrahydroquinolin-4-yl]acetamide (150 mg, 0.32 mmol) was dissolved in DMF at room temperature and Cs2CO3 (259 mg, 0.80 mmol) was added. Methyl 4-bromo-2,2-dimethylbutanoate (157 mg, 0.48 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was concentrated under reduced pressure. The residue was partitioned between ethyl acetate and water, then extracted three times with ethyl acetate, dried over MgSO4, filtered and concentrated. The crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system) to afford the product (118 mg, 61%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and water
  3. extractionextracted three times with ethyl acetate
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude residue was purified by silica gel chromatography (hexanes-ethyl acetate system)

Sources & evidence

ORD record
ord-89a3a2907acd4c60942e8903b4fca9a9
Source dataset
uspto-grants-2009_03
Patent number
US07504508B2

Reaction notes

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