Potassium Carbonate → 7-(Cyanomethoxy)indole

HRID 1198562

Reaction equation

HRID 1198562 reaction equation
Cl[C:2]1[CH:11]=[C:10]2[C:5](C=C[C:8](/[CH:12]=C/C3C=C(C=CC=3)CO)=[N:9]2)=[CH:4][CH:3]=1.Br[CH2:23][C:24]#[N:25].C(=O)([O-])[O-:27].[K+].[K+]>CO.C1(C)C=CC=CC=1.[OH-].[OH-].[Pd+2]>[C:24]([CH2:23][O:27][C:5]1[CH:4]=[CH:3][CH:2]=[C:11]2[C:10]=1[NH:9][CH:8]=[CH:12]2)#[N:25]

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11534BromoacetonitrileHCID 10827738trans-3-[2-(7-Chloroquinolin-2-yl)ethenyl]benzyl alcohol

Product 1

HCID 150540207-(Cyanomethoxy)indole

Reagents, catalysts & solvents 3

HCID 9942167Palladium hydroxideCatalystHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

The protected 7-substituted indole (Example 34a part ii) (0.53 g, 1.75 mmol) in methanol (10 ml) and toluene (10 ml) was hydrogenated in a Parr apparatus at 50 p.s.i. for 1 hour in the presence of Pearlman's catalyst (0.33 g). The reaction mixture was filtered through Celite and the filtrate evaporated in vacuo. The crude 7-hydroxy indole was taken up in methyl ethyl ketone (20 ml), and bromoacetonitrile (0.65 g, 5.25 mmol) and anhydrous potassium carbonate (0.6 g, 4.35 mmol) added. The mixture was refluxed under nitrogen for 1 hour, cooled, poured into 2.5M hydrochloric acid/ice and extracted into dichloromethane. The organic phase was washed with water, dried, filtered and evaporated in vacuo.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. customthe filtrate evaporated in vacuo
  3. temperatureThe mixture was refluxed under nitrogen for 1 hour
  4. temperaturecooled
  5. extractionextracted into dichloromethane
  6. washThe organic phase was washed with water
  7. customdried
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-cfb28e7ed3b24622adf9dc9b1f6170ad
Source dataset
uspto-grants-1994_01
Patent number
US05281593

Linked notes

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