Cesium fluoride → 1-Phenylindolin-5-yl 4-isopropylphenylcarbamate

HRID 2360162Notes

Reaction equation

HRID 2360162 reaction equation
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][C:11](=[O:22])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[NH:18][CH2:17][CH2:16]3)=[CH:6][CH:5]=1)([CH3:3])[CH3:2].FC(F)(F)S(O[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[Si](C)(C)C)(=O)=O.[F-].[Cs+]>C(#N)C.C(OCC)(=O)C>[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([NH:10][C:11](=[O:22])[O:12][C:13]2[CH:14]=[C:15]3[C:19](=[CH:20][CH:21]=2)[N:18]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH2:17][CH2:16]3)=[CH:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 33840072-(Trimethylsilyl)phenyl trifluoromethanesulfonateHCID 86659865Indolin-5-yl 4-isopropylphenylcarbamate

Product 1

HCID 866598831-Phenylindolin-5-yl 4-isopropylphenylcarbamateYield 8.2%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of indolin-5-yl 4-isopropylphenylcarbamate (50 mg, 0.17 mmol) in 3.4 mL of acetonitrile was added 2-(trimethylsilyl)phenyl trifluoromethanesulfonate (41 μL, 0.17 mmol) and caesium fluoride (51 mg, 0.34 mmol) at room temperature, successively. After the reaction mixture was stirred at the same temperature overnight, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, and dried over MgSO4. After filtration, the filtrate was concentrated in vacuo, and the residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20) to obtain the title compound as a white solid (5.2 mg, 8%).

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationAfter filtration
  4. concentrationthe filtrate was concentrated in vacuo
  5. customthe residue was purified by silica gel column chromatography (hexane/ethyl acetate=95/5 to 80/20)

Sources & evidence

ORD record
ord-e5d00d2e366e47d6a968b8628f6e52a5
Source dataset
uspto-grants-2014_04
Patent number
US08686024B2

Reaction notes

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