Water → HCID 69490095, compound

HRID 1271860Notes

Reaction equation

HRID 1271860 reaction equation
[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([O:26]CC=C)=[CH:21][CH:20]=2)=[O:16])([CH3:4])([CH3:3])[CH3:2].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C([O-])(O)=O.[Na+]>CO.[Cl-].[Na+].O.[Pd]>[C:1]([O:5][C:6](=[O:30])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][C:22]([OH:26])=[CH:21][CH:20]=2)=[O:16])([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 516892Sodium BicarbonateHCID 69490219HCID 69490219, compound

Product 1

HCID 69490095HCID 69490095, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 3370 mg (8.27 mmol) {2-[(5-Allyloxy-1H-indole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (36) in 100 ml methanol was added 5 ml water, 750 mg Pd (10% on C) and 300 mg p-toluenesulfonic acid. After heating at reflux for 6 h the reaction mixture was added to a 1:1 mixture of brine and saturated NaHCO3 solution. The aqueous phase was extracted twice with ethyl acetate and the combined organic phases were washed with brine, dried over Na2SO4 and filtrated over celite. The solvent was removed and the residue was subjected to silica gel chromatography (petrolether/ethyl acetate 2:1). {2-[(5-Hydroxy-1H-indole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (37) was recrystallized from diethyl ether/petrol ether to yield 1265 mg (3.44 mmol) crystalls, mp. 197° C. (decomposition).

Workup

  1. temperatureAfter heating
  2. temperatureat reflux for 6 h the reaction mixture
  3. extractionThe aqueous phase was extracted twice with ethyl acetate
  4. washthe combined organic phases were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltrated over celite
  7. customThe solvent was removed
  8. custom{2-[(5-Hydroxy-1H-indole-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (37) was recrystallized from diethyl ether/petrol ether
  9. customto yield 1265 mg (3.44 mmol) crystalls, mp. 197° C. (decomposition)

Sources & evidence

ORD record
ord-6f17a70ed2254722877c3a9806fd840f
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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