Water → 4-((6-Ethoxy-1H-indol-5-yl)oxy)pyridin-2-amine

HRID 1427015Notes

Reaction equation

HRID 1427015 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][C:5]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH:20]C(=O)C)[CH:15]=1)[CH3:2].[OH-].[Na+].O.C(OCC)(=O)C>CO>[CH2:1]([O:3][C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[CH:9][NH:10]2)=[CH:6][C:5]=1[O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([NH2:20])[CH:15]=1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 86730318N-(4-((6-Ethoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide

Product 1

HCID 867303194-((6-Ethoxy-1H-indol-5-yl)oxy)pyridin-2-amineYield 86%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
75 °C

Procedure

N-(4-((6-ethoxy-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 15-5 (7.16 g, 23.0 mmol) was dissolved in methanol (50 mL), a 2 M sodium hydroxide solution (50 mL) was added under nitrogen atmosphere at room temperature, and the mixture was heated and stirred at 75° C. for 2.5 hours. The reaction mixture was cooled to room temperature and then water and ethyl acetate were added for partition. The aqueous layer was extracted with ethyl acetate and the combined organic layer was washed with a saturated saline solution. The organic layer was dried over anhydrous magnesium sulfate, then the resultant was filtered and concentrated under vacuum. A liquid mixture of diethyl ether and ethyl acetate was added to the residue, and the mixture was collected by filteration and washed to obtain the title compound (5.35 g, 86%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe reaction mixture was cooled to room temperature
  3. customfor partition
  4. extractionThe aqueous layer was extracted with ethyl acetate
  5. washthe combined organic layer was washed with a saturated saline solution
  6. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  7. filtrationthe resultant was filtered
  8. concentrationconcentrated under vacuum
  9. additionA liquid mixture of diethyl ether and ethyl acetate
  10. additionwas added to the residue
  11. customthe mixture was collected by filteration
  12. washwashed

Sources & evidence

ORD record
ord-f2bbdf2c1936413ca68f54c711e569b5
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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