Sodium Hydroxide → 4-((6-(2-Ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amine

HRID 1427040Notes

Reaction equation

HRID 1427040 reaction equation
[OH-].[Na+].[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH:25]C(=O)C)[CH:20]=1)[CH3:4]>CO.C(OCC)(=O)C.O>[CH2:3]([O:5][CH2:6][CH2:7][O:8][C:9]1[CH:17]=[C:16]2[C:12]([CH:13]=[CH:14][NH:15]2)=[CH:11][C:10]=1[O:18][C:19]1[CH:24]=[CH:23][N:22]=[C:21]([NH2:25])[CH:20]=1)[CH3:4]

Participants

6

Reactant 2

HCID 14798Sodium HydroxideHCID 86730342N-(4-((6-(2-Ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide

Product 1

HCID 867303434-((6-(2-Ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-amineYield 87%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

A 2 M sodium hydroxide solution (20 mL) was added to a solution of N-(4-((6-(2-ethoxyethoxy)-1H-indol-5-yl)oxy)pyridin-2-yl)acetamide described in Production Example 24-6 (2.5 g, 7.04 mmol) in methanol (20 mL) under nitrogen atmosphere at room temperature, and the mixture was heated and stirred under reflux at 75° C. for 2 hours. The reaction liquid was allowed to stand to cool to room temperature and then diluted with ethyl acetate and water. The organic layer was washed with a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and then the filtrate was concentrated under vacuum. The resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:9-0:1-ethyl acetate:methanol=49:1-24:1) to obtain the title compound (1.92 g, 87%).

Workup

  1. temperaturethe mixture was heated
  2. customThe reaction liquid
  3. temperatureto cool to room temperature
  4. washThe organic layer was washed with a saturated saline solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe drying agent was separated by filtration
  7. concentrationthe filtrate was concentrated under vacuum
  8. customThe resultant residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=1:9-0:1-ethyl acetate:methanol=49:1-24:1)

Sources & evidence

ORD record
ord-43f451f4af754f318978d73a2566045f
Source dataset
uspto-grants-2015_01
Patent number
US08933099B2

Reaction notes

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