Sodium borohydride → HCID 66852723, compound

HRID 505624Notes

Reaction equation

HRID 505624 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH:20]=[O:21])=[CH:12]1)(=[O:10])=[O:9].[BH4-].[Na+]>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([N:11]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=2)[C:13]([CH2:20][OH:21])=[CH:12]1)(=[O:9])=[O:10]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 86613141HCID 86613141, compound

Product 1

HCID 66852723HCID 66852723, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a three-necked round bottom flask equipped with pressure equalizing funnel, 1-(2-Bromobenzenesulfonyl)-1H-indole-3-carboxaldehyde (D27 3.63 g, 0.01 mole) and dichloromethane (8 mL) were taken. Sodiumborohydride (0.005-0.01 mole) was added slowly at room temperature and the reaction mixture was stirred well for next 3-4 hours. After the completion of reaction (TLC, 3-5 hours), the product was isolated by distillation under reduced pressure. The residue was extracted with ethyl acetate (2×25 mL). The combined organic extracts were washed with water, followed by brine, dried over anhydrous sodium sulfate. The organic layer was evaporated under vacuum. The residue was generally an oily liquid, which was isolated and purified by flash chromatography (silica gel, EtOAc/Hexane, 2/8) to afford the title compound, which was identified by IR, NMR and mass spectral analyses.

Workup

  1. customIn a three-necked round bottom flask equipped with pressure
  2. customAfter the completion of reaction (TLC, 3-5 hours)
  3. customthe product was isolated by distillation under reduced pressure
  4. extractionThe residue was extracted with ethyl acetate (2×25 mL)
  5. washThe combined organic extracts were washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. customThe organic layer was evaporated under vacuum
  8. customwhich was isolated
  9. custompurified by flash chromatography (silica gel, EtOAc/Hexane, 2/8)

Sources & evidence

ORD record
ord-00807f92ba36485088eb357022d93beb
Source dataset
uspto-grants-2010_08
Patent number
US07781476B2

Reaction notes

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