Ethyl cyanoacetate → HCID 67107921, compound

HRID 1026614Notes

Reaction equation

HRID 1026614 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].C(O[CH:14](N(C)C)[N:15](C)C)(C)(C)C.N[C:22]1[CH:23]=[C:24]2[C:28](=[CH:29][CH:30]=1)[NH:27][CH:26]=[CH:25]2.C(OCC)(=O)C>C(O)CCC>[CH2:1]([O:3][C:4]([C:5]1[N:15]=[CH:14][N:7]([C:22]2[CH:23]=[C:24]3[C:28](=[CH:29][CH:30]=2)[NH:27][CH:26]=[CH:25]3)[CH:6]=1)=[O:8])[CH3:2]

Participants

6

Reactant 4

HCID 7764Ethyl cyanoacetateHCID 8857Ethyl AcetateHCID 788675-AminoindoleHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 67107921HCID 67107921, compoundYield 17%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of ethylcyanoacetate (1.0 g, 7.75 mmol) and t-butoxy bis(dimethylamino)methane (2.7 g, 15.5 mmol) was stirred for 18 h at room temperature. After distillation under reduced pressure, 5-aminoindole (1.3 g, 7.75 mmol) was added. The mixture was dissolved in n-butanol, and refluxed for 15 h. The reaction solution was cooled, ethyl acetate was added thereto, and washed with aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The resulting solid was filtered, washed with ethyl acetate and dried to give the title compound (0.33 g, 17% Yield).

Workup

  1. additionwas added
  2. temperaturerefluxed for 15 h
  3. temperatureThe reaction solution was cooled
  4. washwashed with aqueous sodium bicarbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. filtrationThe resulting solid was filtered
  8. washwashed with ethyl acetate
  9. customdried

Sources & evidence

ORD record
ord-f7927b1bdca844a08e4eca3095f32757
Source dataset
uspto-grants-2014_05
Patent number
US08729273B2

Reaction notes

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