Sodium Bicarbonate → 3-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-amine

HRID 2196662Notes

Reaction equation

HRID 2196662 reaction equation
O.O.[Sn](Cl)(Cl)(Cl)Cl.[N+:8]([C:11]1[CH:12]=[C:13]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][NH:17][C:14]2=[N:15][CH:16]=1)([O-])=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:8][C:11]1[CH:12]=[C:13]2[C:19]([C:20]([F:23])([F:22])[F:21])=[CH:18][NH:17][C:14]2=[N:15][CH:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 67155904HCID 67155904, compoundHCID 85782573Tin tetrachloride dihydrate

Product 1

HCID 671557463-(Trifluoromethyl)-1H-pyrrolo[2,3-b]pyridin-5-amineYield 63.4%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Tin chloride dihydrate (4.0 g) was added to 5-nitro-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (0.58 g) in ethyl acetate (50 mL). The resulting solution was refluxed for 3 hours. The cooled solution was treated with dilute aqueous sodium bicarbonate. The resulting slurry was filtered through celite, and the filter cake was washed with ethyl acetate. The layers were separated. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated to provide 5-amino-3-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (320 mg, 63%) as a solid.

Workup

  1. temperatureThe resulting solution was refluxed for 3 hours
  2. filtrationThe resulting slurry was filtered through celite
  3. washthe filter cake was washed with ethyl acetate
  4. customThe layers were separated
  5. washThe organic layer was washed with brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-c2e9ea2840f546158bf91f1b7649acbf
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

Loading…