Sodium Iodide → HCID 58755257, compound

HRID 1163325Notes

Reaction equation

HRID 1163325 reaction equation
[C:1]1([C:7]2[NH:8][C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[I-].[Na+].Cl[CH2:21][CH2:22][CH2:23][O:24][C:25]1[CH:38]=[CH:37][C:28]2[CH:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:30][O:31][C:27]=2[CH:26]=1.[Cl-].[NH4+]>CN(C)C=O.O>[C:1]1([C:7]2[N:8]([CH2:21][CH2:22][CH2:23][O:24][C:25]3[CH:38]=[CH:37][C:28]4[CH:29]([CH2:32][C:33]([O:35][CH3:36])=[O:34])[CH2:30][O:31][C:27]=4[CH:26]=3)[C:9]3[C:14]([CH:15]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 136982-PhenylindoleHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 58755248HCID 58755248, compound

Product 1

HCID 58755257HCID 58755257, compoundYield 18%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-phenyl-1H-indole (0.425 g, 2.20 mmol) in N,N-dimethylformamide (2 mL) was added sodium hydride (60% in oil, 88 mg, 2.20 mmol), and the mixture was stirred at room temperature for 30 min. A solution of sodium iodide (0.330 g, 2.20 mmol) and methyl [6-(3-chloropropoxy)-2,3-dihydro-1-benzofuran-3-yl]acetate (0.589 g, 2.07 mmol) in N,N-dimethylformamide (3 mL) was added to the reaction mixture, and the mixture was stirred at room temperature for 18 hr. Water and saturated aqueous ammonium chloride solution were added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane) to give the title compound (0.160 g, yield 18%) as a colorless oil.

Workup

  1. stirringthe mixture was stirred at room temperature for 18 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (10%-40% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-69e11d6c8f42451bb05dc65140a7ab28
Source dataset
uspto-grants-2010_10
Patent number
US07820837B2

Reaction notes

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