Cesium fluoride → HCID 67273517, compound

HRID 1020912Notes

Reaction equation

HRID 1020912 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+].Br[CH2:29][CH2:30][O:31][CH2:32][CH3:33]>C(C#N)(C)=O.C(Cl)Cl>[C:1]1([C:6]2[NH:7][C:8]3[C:13]([CH:14]=2)=[C:12]([O:15][CH2:29][CH2:30][O:31][CH2:32][CH3:33])[CH:11]=[CH:10][CH:9]=3)[CH2:5][CH2:4][CH2:3][CH:2]=1

Participants

6

Reactant 3

HCID 25953Cesium fluorideHCID 611412-Bromoethyl ethyl etherHCID 67273355HCID 67273355, compound

Product 1

HCID 67273517HCID 67273517, compoundYield 74%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 694302-OxopropiononitrileSolvent

Conditions

Temperature
60 °C

Procedure

To 500 mg (1.41 mmol) of 2-cyclopent-1-enyl-4-triisopropylsilyloxy-1H-indole (14d step 1) in 5 mL AcCN was added 255 mg (1.68 mmol, 1.2 eq) of CsF and 479 μL (4.23 mmol, 3 eq) 2-bromoethylethyl ether. The reaction was heated at 60° C. overnight then cooled to rt, diluted with CH2Cl2 and filtered through celite and concentrated. The residue was partitioned between ether and H2O, the ether layer was then washed with aqueous NaCl solution, dried (MgSO4), and concentrated under vacuum to yield 282 mg (74%) of 2-cyclopent-1-enyl-4-(2-ethoxy-ethoxy)-1H-indole.

Workup

  1. temperaturethen cooled to rt
  2. filtrationfiltered through celite
  3. concentrationconcentrated
  4. customThe residue was partitioned between ether and H2O
  5. washthe ether layer was then washed with aqueous NaCl solution
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1fc66664e78d43e88bfc39b0b1ba3586
Source dataset
uspto-grants-2014_05
Patent number
US08716493B2

Reaction notes

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