Water → HCID 58931263, compound

HRID 853353Notes

Reaction equation

HRID 853353 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([O:10][C:11]2[CH:12]=[C:13]3[C:17](=[CH:18][CH:19]=2)[NH:16][CH:15]=[CH:14]3)[CH:7]=[CH:6][N:5]=1.[F:20][CH2:21][CH2:22][NH:23][C:24](=O)[O:25]C1C=CC=CC=1.O>CN(C)C=O>[F:20][CH2:21][CH2:22][NH:23][C:24]([N:16]1[C:17]2[C:13](=[CH:12][C:11]([O:10][C:8]3[CH:7]=[CH:6][N:5]=[C:4]([NH2:3])[CH:9]=3)=[CH:19][CH:18]=2)[CH:14]=[CH:15]1)=[O:25]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 219493654-(1H-5-indolyloxy)-2-pyridinamineHCID 22936733Phenyl (2-fluoroethyl)carbamate

Product 1

HCID 58931263HCID 58931263, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% in oil) (360 mg) was added to a solution of 2.0 g of 5-[(2-amino-4-pyridyl)oxy]-1H-indole in 30 ml of dimethylformamide at room temperature. After stirring for 5 minutes, the mixture was placed in an ice bath and 1.8 g of phenyl N-(2-fluoroethyl)carbamate was added while cooling. The mixture was returned to room temperature and stirred for 30 minutes, after which water was added and extraction was performed with ethyl acetate. The extract was passed through a glass filter coated with silica gel. The ethyl acetate layer was washed once with sodium bicarnobate water and dried over magnesium sulfate. The drying agent was filtered off to obtain 1.93 g of a faint brown powder.

Workup

  1. customthe mixture was placed in an ice bath
  2. temperaturewhile cooling
  3. customwas returned to room temperature
  4. stirringstirred for 30 minutes
  5. extractionextraction
  6. filtrationfilter
  7. washThe ethyl acetate layer was washed once with sodium bicarnobate water
  8. dry with materialdried over magnesium sulfate
  9. filtrationThe drying agent was filtered off

Sources & evidence

ORD record
ord-2c09d768b9fa4200b773f3d30b5111dc
Source dataset
uspto-grants-2007_08
Patent number
US07253286B2

Reaction notes

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