Sodium Carbonate → 4-Bromo-1H-indole-2-carbonitrile

HRID 888905Notes

Reaction equation

HRID 888905 reaction equation
P(Cl)(Cl)(Cl)=O.[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]([C:16]([NH2:18])=O)[NH:11]2.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1>[Br:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[C:10]([C:16]#[N:18])[NH:11]2

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 591512734-bromo-1H-indole-2-carboxamide

Product 1

HCID 591513014-Bromo-1H-indole-2-carbonitrileYield 82.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Phosphorous oxychloride (1.9 mL, 20 mmol) was added to a suspension of 4-bromo-1H-indole-2-carboxylic acid amide (1.32 g, 5.5 mmol.) in toluene (10 mL) and the mixture was stirred at reflux for 45 min. On cooling, the mixture was poured into an aqueous Na2CO3 solution (sat., 50 mL) and the mixture stirred until effervescence had subsided. The layers were separated, the aqueous phase extracted with EtOAc and the combined organic layers dried (MgSO4) and evaporated to dryness. The crude material was purified by column chromatography to afford the title compound as a solid (1.00 g, 82%).

Workup

  1. temperatureat reflux for 45 min
  2. temperatureOn cooling
  3. stirringthe mixture stirred until effervescence
  4. customThe layers were separated
  5. extractionthe aqueous phase extracted with EtOAc
  6. dry with materialthe combined organic layers dried (MgSO4)
  7. customevaporated to dryness
  8. customThe crude material was purified by column chromatography

Sources & evidence

ORD record
ord-8f744deb2a624617a3df05241bc699f3
Source dataset
uspto-grants-2012_08
Patent number
US08252792B2

Reaction notes

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