1-Iodooctane → N-(1-octyl-5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide

HRID 1107967Notes

Reaction equation

HRID 1107967 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][CH:11]=[CH:10]2)=[O:5])[CH3:2].[H-].[Na+].I[CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]>CN(C=O)C>[CH2:28]([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])[CH:10]=[CH:11]1)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 3

HCID 123801-IodooctaneHCID 24758Sodium hydrideHCID 22247308N-(5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide

Product 1

HCID 22247342N-(1-octyl-5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamideYield 52.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N-(5-Ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide (1.45 g) was dissolved in DMF (10 ml) and NaH (P=60%, 132 mg) was added under a nitrogen atmosphere, which was followed by stirring at room temperature for 1 hr. Then, 1-iodooctane (1.06 g) was added and the mixture was stirred at the same temperature for 2 hr. The reaction mixture was poured into ice water. The mixture was extracted with AcOEt (100 ml), 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: benzene/AcOEt-1/0-1/1) to give 1.02 g of N-(1-octyl-5-ethoxycarbonylmethyl-4,6-dimethylindol-7-yl)-2,2-dimethylpropanamide.

Workup

  1. stirringthe mixture was stirred at the same temperature for 2 hr
  2. extractionThe mixture was extracted with AcOEt (100 ml)
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customAcOEt was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: benzene/AcOEt-1/0-1/1)

Sources & evidence

ORD record
ord-3591b35cd3e646e4a7c0f60b65a6e8d9
Source dataset
uspto-grants-2000_05
Patent number
US06063806

Reaction notes

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