Water → HCID 68498210, compound

HRID 1038760Notes

Reaction equation

HRID 1038760 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15][C:16]1[CH:21]=[CH:20][C:19]([NH2:22])=[CH:18][N:17]=1)[CH:9]=2)=[O:5])[CH3:2].[C:23](OC(=O)C)(=[O:25])[CH3:24].O>N1C=CC=CC=1>[CH2:1]([O:3][C:4]([C:6]1[NH:7][C:8]2[C:13]([CH:14]=1)=[CH:12][CH:11]=[C:10]([O:15][C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23](=[O:25])[CH3:24])=[CH:18][N:17]=1)[CH:9]=2)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 68493636HCID 68493636, compound

Product 1

HCID 68498210HCID 68498210, compoundYield 29.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of 6-(5-aminopyridin-2-yloxy)-1H-indole-2-carboxylic acid ethyl ester (2.6 g, 8.6 mmol) in pyridine (13 mL) was added acetic anhydride (2.2 g, 21 mmol) under ice cooling and the mixture was stirred for 2 hours. Water (30 mL) was added to the reaction mixture and extracted with AcOEt, the organic layer was washed with 2 M HCl, saturated aqueous NaHCO3 and brine, dried over anhydrous sodium sulfate and evaporated. The residue was crystallized with 2-propyl alcohol and filtrated to give 0.85 g of the title compound. The filtrate was evaporated and the residue was purified by silica gel column chromatography (n-hexane:AcOEt=1:3) to give 1.26 g (total of 2.11 g) of the title compound as pale yellow crystals.

Workup

  1. extractionextracted with AcOEt
  2. washthe organic layer was washed with 2 M HCl, saturated aqueous NaHCO3 and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customevaporated
  5. customThe residue was crystallized with 2-propyl alcohol
  6. filtrationfiltrated

Sources & evidence

ORD record
ord-fc78ecfaf96942c881d1e256968cb3d5
Source dataset
uspto-grants-2013_10
Patent number
US08551999B2

Reaction notes

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