Sodium hydride → HCID 23143999, compound

HRID 2357105Notes

Reaction equation

HRID 2357105 reaction equation
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[NH:4][CH:3]=1.[H-].[Na+].Cl[CH:17]1[O:21][CH:20]([CH2:22][O:23][C:24](=[O:32])[C:25]2[CH:30]=[CH:29][C:28]([CH3:31])=[CH:27][CH:26]=2)[CH:19]([O:33][C:34](=[O:42])[C:35]2[CH:40]=[CH:39][C:38]([CH3:41])=[CH:37][CH:36]=2)[CH2:18]1>C(#N)C>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([N+:11]([O-:13])=[O:12])[CH:9]=2)[N:4]([CH:17]2[O:21][CH:20]([CH2:22][O:23][C:24](=[O:32])[C:25]3[CH:26]=[CH:27][C:28]([CH3:31])=[CH:29][CH:30]=3)[CH:19]([O:33][C:34](=[O:42])[C:35]3[CH:36]=[CH:37][C:38]([CH3:41])=[CH:39][CH:40]=3)[CH2:18]2)[CH:3]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2881283,5-Di-O-(p-toluyl)-2-deoxy-D-ribofuranosyl chlorideHCID 231439973-Iodo-5-nitro-1H-indole

Product 1

HCID 23143999HCID 23143999, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1.0 g (3.5 mmol) 3-iodo-5-nitroindole in 15 ml acetonitrile were added 0.16 g (6.7 mmol) sodium hydride (Aldrich 223441-50G). The stirring was continued and the suspension turned red. After 15 min. 2.02 g (5.2 mmol) 5-chloro-2-(4-methyl-benzoyloxymethyl)-3-(4-methyl-benzoyloxy)-tetrahydro-furan were added in small portions and the stirring was continued for another 60 minutes at room temperature. The precipitate was removed by filtration and washed once with acetonitrile. The combined yellow filtrates were concentrated until a product precipitated. For complete precipitation of the product 50 ml ethanol were added. The yellow precipitate was removed by filtration und washed with ethanol. The residuum was dried over phosphorus pentoxide and potassium hydroxide in a vacuum (yield: 1.9 g).

Workup

  1. waitthe stirring was continued for another 60 minutes at room temperature
  2. customThe precipitate was removed by filtration
  3. washwashed once with acetonitrile
  4. concentrationThe combined yellow filtrates were concentrated until a product
  5. customprecipitated
  6. customFor complete precipitation of the product 50 ml ethanol
  7. additionwere added
  8. customThe yellow precipitate was removed by filtration
  9. washund washed with ethanol
  10. dry with materialThe residuum was dried over phosphorus pentoxide and potassium hydroxide in a vacuum (yield: 1.9 g)

Sources & evidence

ORD record
ord-476b9c4594674563a154509b78a1468c
Source dataset
uspto-grants-2010_07
Patent number
US07759470B2

Reaction notes

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