Sodium hydride → HCID 70032910, compound

HRID 434020

Reaction equation

HRID 434020 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4].[CH2:21]1[O:25][C:24]2[CH:26]=[C:27]([Cl:32])[C:28]([CH2:30]Cl)=[CH:29][C:23]=2[O:22]1>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C>[CH2:3]([O:5][C:6]([C:8]1[N:9]([CH2:30][C:28]2[C:27]([Cl:32])=[CH:26][C:24]3[O:25][CH2:21][O:22][C:23]=3[CH:29]=2)[C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][CH:19]=[CH2:20])=[CH:12][CH:11]=2)=[O:7])[CH3:4]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 901136-Chloropiperonyl chlorideHCID 13286893Ethyl 5-[(prop-2-en-1-yl)oxy]-1H-indole-2-carboxylate

Product 1

HCID 70032910HCID 70032910, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

To a mixture of NaH (60% suspension in mineral oil, 0.24 g, 6.12 mmol) and DMF (20 mL) was added 5-allyloxyindole-2-carboxylic acid ethyl ester (1.0 g, 4.08 mmol), from Example 1(d). After stirring at room temperature for 1 h, 6-chloropiperonyl chloride (0.84 g, 4.08 mmol) was added followed by the addition of tetrabutyl ammonium iodide (0.15 g, 0.41 mmol). The reaction was stirred at room temperature for 18 h. When the reaction was complete as indicated by TLC, the reaction mixture was partitioned between EtOAc and water. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed in vacuo and the resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes) to yield the desired product as an oil (0.72 g, 43%). LC/MS (ES+) m/e 414.0 [M+H]+.

Workup

  1. stirringThe reaction was stirred at room temperature for 18 h
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried (Na2SO4)
  5. customThe solvent was removed in vacuo
  6. customthe resulting crude product was purified by flash column chromatography (silica gel, EtOAc/hexanes)

Sources & evidence

ORD record
ord-b1232f5cd63a4771b76d4c4fa67413d4
Source dataset
uspto-grants-2003_12
Patent number
US06670388B1

Linked notes

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