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Potassium Carbonate → (E)-tert-butyl 3-(3-(1-isopropyl-2-(4-(2-methoxyethoxy)benzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate

HRID 1401071
Notes
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Reaction equation

HRID 1401071 reaction equation
[CH:1]([N:4]([C:16](=[O:35])/[CH:17]=[CH:18]/[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH:20]=1)[NH:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].BrC[CH2:44][O:45][CH3:46]>CC(C)=O>[CH:1]([N:4]([C:16](=[O:35])/[CH:17]=[CH:18]/[C:19]1[C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[CH:20]=1)[NH:5][C:6](=[O:15])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][CH2:44][O:45][CH3:46])=[CH:9][CH:8]=1)([CH3:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 809722-Bromoethyl methyl etherHCID 71468219HCID 71468219, compound

Product 1

HCID 71468331(E)-tert-butyl 3-(3-(1-isopropyl-2-(4-(2-methoxyethoxy)benzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

To solution containing (E)-tert-butyl 3-(3-(1-isopropyl-2-(4-methoxybenzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate (100.0 mg, 0.22 mmol) and K2CO3 (35.8 mg, 0.26 mmol) dissolved in acetone (5.0 ml), 1-bromo-2-methoxyethane (0.024 ml, 0.26 mmol) was added drop-wise. The reaction mixture was refluxed at 60° C. for 48 hr. After concentration under reduced pressure, the solution was separated through silica gel chromatography (CHCl3: methanol=65:1) so that ivory solid form of (E)-tert-butyl 3-(3-(1-isopropyl-2-(4-(2-methoxyethoxy)benzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate was obtained (66.4 mg, 59%).

Workup

  1. concentrationAfter concentration under reduced pressure
  2. customthe solution was separated through silica gel chromatography (CHCl3: methanol=65:1) so that ivory solid form of (E)-tert-butyl 3-(3-(1-isopropyl-2-(4-(2-methoxyethoxy)benzoyl)hydrazinyl)-3-oxoprop-1-enyl)-1H-indole-1-carboxylate
  3. customwas obtained (66.4 mg, 59%)

Sources & evidence

ORD record
ord-bf1f5696aa0e4e009a1734b27f0207ee
Source dataset
uspto-grants-2014_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08906952B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes