HCID 59398526, compound → HCID 22936495, compound

HRID 2070016Notes

Reaction equation

HRID 2070016 reaction equation
C(OC[N:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[C:13]2[CH:12]=[CH:11]1)C1C=CC=CC=1>CO.Cl.[C].[Pd]>[NH:10]1[C:14]2=[N:15][CH:16]=[CH:17][C:18]([O:19][C:20]3[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=3)=[C:13]2[CH:12]=[CH:11]1

Participants

5

Reactant 1

HCID 59398526HCID 59398526, compound

Product 1

HCID 22936495HCID 22936495, compoundYield 75.3%

Reagents, catalysts & solvents 3

HCID 178418390HCID 178418390, compoundCatalystHCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

4-(1-Benzyloxymethyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (21.3 g, 61.7 mmol) was dissolved in methanol (300 mL) and 10 N hydrochloric acid (20 mL), and palladium carbon (10%, 800 mg) was added thereto. The resulting mixture was stirred under a hydrogen atmosphere at 50° C. for 7 hours. The catalyst was removed by celite filtration, and the resulting methanol solution was concentrated. The residue was added to THF (500 mL) and a 5 N sodium hydroxide aqueous solution (100 mL), and the resulting mixture was stirred. The solid was immediately dissolved, and the reaction solution was separated into two layers. The solution was subsequently stirred at room temperature for 3 hours, and saturated brine (300 mL) was added thereto. The THF layer was isolated and washed with saturated brine (100 mL). The organic layer was dried over anhydrous sodium sulfate and then concentrated. The residue was purified by amino-silica gel (Fuji Silysia, 1 L of ethyl acetate) to give 4-(1H-pyrrolo[2,3-b]pyridin-4-yloxy)aniline (10.46 g, yield: 75%).

Workup

  1. customThe catalyst was removed by celite filtration
  2. concentrationthe resulting methanol solution was concentrated
  3. additionThe residue was added to THF (500 mL)
  4. stirringa 5 N sodium hydroxide aqueous solution (100 mL), and the resulting mixture was stirred
  5. dissolutionThe solid was immediately dissolved
  6. customthe reaction solution was separated into two layers
  7. stirringThe solution was subsequently stirred at room temperature for 3 hours
  8. additionsaturated brine (300 mL) was added
  9. customThe THF layer was isolated
  10. washwashed with saturated brine (100 mL)
  11. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  12. concentrationconcentrated
  13. customThe residue was purified by amino-silica gel (Fuji Silysia, 1 L of ethyl acetate)

Sources & evidence

ORD record
ord-52262f4dcbc243d3a123e12668906a13
Source dataset
uspto-grants-2012_10
Patent number
US08299252B2

Reaction notes

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