Trifluoroacetic acid → 5-(1H-pyrrol-1-yl)pyridin-3-amine

HRID 340458Notes

Reaction equation

HRID 340458 reaction equation
C(O)(C(F)(F)F)=O.C(OC(=O)[NH:14][C:15]1[CH:16]=[N:17][CH:18]=[C:19]([N:21]2[CH:25]=[CH:24][CH:23]=[CH:22]2)[CH:20]=1)(C)(C)C>C(Cl)(Cl)Cl>[N:21]1([C:19]2[CH:20]=[C:15]([NH2:14])[CH:16]=[N:17][CH:18]=2)[CH:22]=[CH:23][CH:24]=[CH:25]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 89546780tert-butyl(5-(1H-pyrrol-1-yl)pyridin-3-yl)carbamate

Product 1

HCID 665215025-(1H-pyrrol-1-yl)pyridin-3-amineYield 104.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

TFA (1 ml) was added to a chloroform (1 ml) solution containing tert-butyl(5-(1H-pyrrol-1-yl)pyridin-3-yl)carbamate (36 mg) obtained in the 1st step, followed by stirring at room temperature for 1 hour. Then, the solvent was distilled away under reduced pressure and the residue was added to a mixture of chloroform, water, and a 1M sodium hydroxide aqueous solution, followed by extraction with chloroform. The resultant was dried over anhydrous sodium sulfate, the solvent was distilled away under reduced pressure, and a light brown solid of 5-(1H-pyrrol-1-yl)pyridin-3-amine (23 mg) was thus obtained.

Workup

  1. customobtained in the 1st step
  2. distillationThen, the solvent was distilled away under reduced pressure
  3. additionthe residue was added to a mixture of chloroform, water
  4. extractiona 1M sodium hydroxide aqueous solution, followed by extraction with chloroform
  5. dry with materialThe resultant was dried over anhydrous sodium sulfate
  6. distillationthe solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-07ebdf1b92cc40f28d1d8cb768305951
Source dataset
uspto-grants-2014_11
Patent number
US08895585B2

Reaction notes

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