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Ethyl Acetate → N-(1-Octyl-5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1107949
Notes
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Reaction equation

HRID 1107949 reaction equation
[CH2:1]([O:3][C:4]([CH2:6][C:7]1[C:8]([CH3:24])=[C:9]2[C:13](=[C:14]([NH:17][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[C:15]=1[CH3:16])[NH:12][CH2:11][CH2:10]2)=[O:5])[CH3:2].I[CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>CN(C=O)C>[CH2:26]([N:12]1[C:13]2[C:9](=[C:8]([CH3:24])[C:7]([CH2:6][C:4]([O:3][CH2:1][CH3:2])=[O:5])=[C:15]([CH3:16])[C:14]=2[NH:17][C:18](=[O:23])[C:19]([CH3:20])([CH3:22])[CH3:21])[CH2:10][CH2:11]1)[CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 123801-IodooctaneHCID 12112203N-(5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 15895566N-(1-Octyl-5-ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamideYield 74.8%

Reagents, catalysts & solvents

1
HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

N-(5-Ethoxycarbonylmethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide (3.5 g) was dissolved in DMF (15 ml), and 1-iodooctane (5.0 g) and K2CO3 (2.9 g) were added, which was followed by stirring under a nitrogen atmosphere at 50° C. for 2 hr. AcOEt (200 ml) was added, and the mixture was washed with water and dried over anhydrous sodium sulfate. AcOEt was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=1/0 -50/1) to give 3.5 g of the title compound.

Workup

  1. washthe mixture was washed with water
  2. dry with materialdried over anhydrous sodium sulfate
  3. customAcOEt was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (eluent: CHCl3 /MeOH=1/0 -50/1)

Sources & evidence

ORD record
ord-66bc2dec6dc949b38409e8d7b0b690ed
Source dataset
uspto-grants-2000_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06063806

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes