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Water → 1-ethyl-6-isopropoxy-2-[4-(2-oxo-oxazolidin-3-yl)-phenyl]-1H-indole-3-carbonitrile

HRID 502211
Notes
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Reaction equation

HRID 502211 reaction equation
Cl[CH2:2][CH2:3][O:4][C:5](=[O:30])[NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:14]([CH2:28][CH3:29])[C:15]3[C:20]([C:21]=2[C:22]#[N:23])=[CH:19][CH:18]=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=3)=[CH:9][CH:8]=1.C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C>[CH2:28]([N:14]1[C:15]2[C:20](=[CH:19][CH:18]=[C:17]([O:24][CH:25]([CH3:27])[CH3:26])[CH:16]=2)[C:21]([C:22]#[N:23])=[C:13]1[C:10]1[CH:11]=[CH:12][C:7]([N:6]2[CH2:2][CH2:3][O:4][C:5]2=[O:30])=[CH:8][CH:9]=1)[CH3:29]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 59425654HCID 59425654, compound

Product 1

HCID 594257571-ethyl-6-isopropoxy-2-[4-(2-oxo-oxazolidin-3-yl)-phenyl]-1H-indole-3-carbonitrileYield 81%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [4-(3-cyano-1-ethyl-6-isopropoxy-1H-indol-2-yl)-phenyl]-carbamic acid 2-chloro-ethyl ester (30 mg, 0.07 mmol) in DMF (1 mL) is added aqueous K2CO3 (10 mg) and then stirred at 50° C. for 18 h. The reaction mixture is poured into cold water and the precipitate collected by filtration and washed with hexane and dried in vacuo to afford the title compound (21 mg, 81%).

Workup

  1. filtrationthe precipitate collected by filtration
  2. washwashed with hexane
  3. customdried in vacuo

Sources & evidence

ORD record
ord-b03890ae156e482690df2deea75b54b6
Source dataset
uspto-grants-2010_08
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07772271B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes