Water → N1-Phenyl-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamide

HRID 387809Notes

Reaction equation

HRID 387809 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.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.O>CN(C)C=O>[C:20]1([NH:26][C:27]([N:16]2[C:17]3[C:13](=[CH:12][C:11]([O:10][C:8]4[CH:7]=[CH:6][N:5]=[C:4]([NH2:3])[CH:9]=4)=[CH:19][CH:18]=3)[CH:14]=[CH:15]2)=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7672Phenyl isocyanateHCID 24758Sodium hydrideHCID 219493654-(1H-5-indolyloxy)-2-pyridinamine

Product 1

HCID 21949159N1-Phenyl-5-[(2-amino-4-pyridyl)oxy]-1H-1-indolecarboxamideYield 74.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

After adding 28 mg of sodium hydride (60% in oil) to a solution of 3.0 g of 5-[(2-amino-4-pyridyl)oxy]-1H-indole in dimethylformamide at room temperature and stirring the mixture for 5 minutes, 1.6 g of phenyl isocyanate was added and the mixture was stirred for 20 minutes. Water was added, extraction was performed with ethyl acetate and the organic layer was washed with water, and then silica gel was added and the solvent was distilled off under reduced pressure. The silica gel was charged into a dry column packed with silica gel and purified by column chromatography (ethyl acetate), to obtain 3.4 g of a colorless powder.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. extractionextraction
  3. washthe organic layer was washed with water
  4. additionsilica gel was added
  5. distillationthe solvent was distilled off under reduced pressure
  6. additionThe silica gel was charged into a dry column
  7. custompurified by column chromatography (ethyl acetate)

Sources & evidence

ORD record
ord-4318ad9d03ec412db15b179a5d758d1a
Source dataset
uspto-grants-2013_02
Patent number
US08372981B2

Reaction notes

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