Ethyl bromoacetate → HCID 67273858, compound

HRID 1020913Notes

Reaction equation

HRID 1020913 reaction equation
[C:1]1([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[C:12]([O:15][Si](C(C)C)(C(C)C)C(C)C)[CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][CH2:3][CH:2]=1.[F-].[Cs+].[CH2:28]([O:30][C:31](=[O:34])[CH2:32]Br)[CH3:29]>C(C#N)(C)=O.C(Cl)Cl>[CH2:28]([O:30][C:31](=[O:34])[CH2:32][O:15][C:12]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:13]=1[CH:14]=[C:6]([C:1]1[CH2:5][CH2:4][CH2:3][CH:2]=1)[NH:7]2)[CH3:29]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 25953Cesium fluorideHCID 67273355HCID 67273355, compound

Product 1

HCID 67273858HCID 67273858, compoundYield 99.1%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
50 °C

Procedure

To 300 mg (0.845 mmol) of 2-cyclopent-1-enyl-4-triisopropylsilyloxy-1H-indole (14d step 1) in 3 mL AcCN was added 154 mg (1.01 mmol, 1.2 eq) of CsF and 282 μL (2.54 mmol, 3 eq) ethylbromoacetate and the reaction was stirred at 50° C. overnight. The reaction was diluted with CH2Cl2 and filtered through celite. The CH2Cl2 layer was washed with 2N Na2CO3 solution, H2O, aqueous NaCl solution, dried (Na2SO4), and concentrated in vacuole to yield 239 mg (99%) of (2-cyclopent-1-enyl-1H-indol-4-yloxy)-acetic acid ethyl ester as a dark oil.

Workup

  1. filtrationfiltered through celite
  2. washThe CH2Cl2 layer was washed with 2N Na2CO3 solution, H2O, aqueous NaCl solution
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuole

Sources & evidence

ORD record
ord-88f74b0ac53142dbbd2d3285b2b121bd
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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