Tetrabutylammonium Fluoride → 2-Tert-butyl-5-nitro-1H-indole-7-carbonitrile

HRID 468349Notes

Reaction equation

HRID 468349 reaction equation
[NH2:1][C:2]1[C:9]([C:10]#[C:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:8][C:7]([N+:16]([O-:18])=[O:17])=[CH:6][C:3]=1[C:4]#[N:5].CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[C:12]([C:11]1[NH:1][C:2]2[C:9]([CH:10]=1)=[CH:8][C:7]([N+:16]([O-:18])=[O:17])=[CH:6][C:3]=2[C:4]#[N:5])([CH3:15])([CH3:13])[CH3:14]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 591292522-Amino-3-(3,3-dimethylbut-1-ynyl)-5-nitrobenzonitrile

Product 1

HCID 534211842-Tert-butyl-5-nitro-1H-indole-7-carbonitrileYield 51.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-amino-3-(3,3-dimethylbut-1-ynyl)-5-nitrobenzonitrile (1.7 g, 7.0 mmol) in THF (35 mL) was added TBAF (9.5 g, 28 mmol) at room temperature. The mixture was heated at reflux overnight. The reaction mixture was cooled and the THF was removed under reduced pressure. Water (50 ml) was added to the residue and the mixture was extracted with EtOAc. The organics were dried over Na2SO4 and the solvent was evaporated under vacuum to obtain 0.87 g of crude product 2-tert-butyl-5-nitro-1H-indole-7-carbonitrile which was used directly in the next step without purification.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. temperatureThe reaction mixture was cooled
  4. customthe THF was removed under reduced pressure
  5. additionWater (50 ml) was added to the residue
  6. extractionthe mixture was extracted with EtOAc
  7. dry with materialThe organics were dried over Na2SO4
  8. customthe solvent was evaporated under vacuum

Sources & evidence

ORD record
ord-72d273dbc18c4b18813d71e847135dac
Source dataset
uspto-grants-2014_01
Patent number
US08623905B2

Reaction notes

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