Water → HCID 15551263, compound

HRID 382029Notes

Reaction equation

HRID 382029 reaction equation
[O:1]=[C:2]1[C:10](=[CH:11][C:12]2[NH:13][CH:14]=[CH:15][CH:16]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][C:8]=2[C:17]2[CH:18]=[C:19]([NH:23][C:24]([C:26]3[CH:31]=[CH:30][C:29]([O:32]C(=O)OC)=[CH:28][CH:27]=3)=[O:25])[CH:20]=[CH:21][CH:22]=2)[NH:3]1.O.[OH-].[K+]>O1CCOCC1>[O:1]=[C:2]1[NH:3][C:4]2[C:9](/[C:10]/1=[CH:11]/[C:12]1[NH:13][CH:14]=[CH:15][CH:16]=1)=[C:8]([C:17]1[CH:18]=[C:19]([NH:23][C:24](=[O:25])[C:26]3[CH:27]=[CH:28][C:29]([OH:32])=[CH:30][CH:31]=3)[CH:20]=[CH:21][CH:22]=1)[CH:7]=[CH:6][CH:5]=2

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 53693749HCID 53693749, compound

Product 1

HCID 15551263HCID 15551263, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A solution of the crude carbonic acid methyl ester 4-[3-[2-oxo-3-[(1H-pyrrol-2-yl)methylene]-2,3-dihydro-1H-indol-4-yl]-phenylcarbamoyl]-phenyl ester (90 mg, 0.194 mmol) in 2 mL of 1,4-dioxane (Aldrich) was treated with 1.5 mL of distilled water and then powdered potassium hydroxide (25 mg, 0.445 mmol) . The reaction mixture was heated at 90° C. for 1 h. The reaction mixture was then allowed to cool to room temperature and directly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 45% ethyl acetate-hexanes elution) to provide a crude yellow solid containing the desired product and a 1,3-dicyclohexylcarbodiimide derivative. Most of the 1,3-dicyclohexylcarbodiimide derivative was removed by precipitation from an ethanolic solution through the slow addition of distilled water. The precipitated solid was collected by suction filtration. The filtrate was concentrated in vacuo and then directly purified by column chromatography. Two additional rounds of flash chromatography (Merck Silica gel 60, 230-400 mesh, 25% ethyl acetate-hexanes elution each) provided pure (Z)-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenyl]-4-hydroxybenzamide (yield: 49 mg, 60%) as a yellow solid (mp 236-238° C.).

Workup

  1. temperatureto cool to room temperature
  2. customdirectly purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 45% ethyl acetate-hexanes elution)
  3. customto provide a crude yellow solid

Sources & evidence

ORD record
ord-9e817e132c7f450093fbae90ec129c09
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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