Water → HCID 67156000, compound

HRID 2196726Notes

Reaction equation

HRID 2196726 reaction equation
[OH-].[Na+].[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[N:12](C(OC)=O)[C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4].O.C(OCC)(=O)C>C1COCC1.CO>[N+:3]([C:6]1[CH:7]=[C:8]2[CH:14]=[C:13]([C:15]([F:18])([F:17])[F:16])[NH:12][C:9]2=[N:10][CH:11]=1)([O-:5])=[O:4]

Participants

7

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 67156200HCID 67156200, compound

Product 1

HCID 67156000HCID 67156000, compoundYield 87.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

Sodium hydroxide (4.2 mL, 4.2 mmol, 1M in water) was added to a solution of methyl 5-nitro-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (0.35 g, 1.19 mmol) in THF (6.9 mL) and methanol (1.7 mL) at room temperature. The reaction mixture was heated at 40° C. for 30 minutes. The reaction mixture was then cooled down and treated with water and ethyl acetate. The layers were then separated. The organic layers were washed twice with water, dried over sodium sulfate, filtered, and evaporated to afford 5-nitro-2-(trifluoromethyl)-1H-pyrrolo[2,3-b]pyridine (0.24 g, 86%), which was carried to the next step without further purification.

Workup

  1. temperatureThe reaction mixture was then cooled down
  2. customThe layers were then separated
  3. washThe organic layers were washed twice with water
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-c1864eec90224cdf96c44352f7121318
Source dataset
uspto-grants-2012_12
Patent number
US08338452B2

Reaction notes

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