Ethyl Acetate → HCID 19887640, compound

HRID 654476Notes

Reaction equation

HRID 654476 reaction equation
[O:1]=[C:2]([CH3:13])[CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5]1.[Cl:14]N1C(=O)CCC1=O.C(OCC)(=O)C>C1COCC1>[Cl:14][C:6]1[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:4]([CH2:3][C:2](=[O:1])[CH3:13])[CH:5]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 31398ChlorosuccinimideHCID 22134407HCID 22134407, compound

Product 1

HCID 19887640HCID 19887640, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-oxopropyl)indole from Example 3, Step 1 (800 mg, 4.6 mmol) in dry THF (20 mL) was added in one portion at r.t. N-chlorosuccinimide (680 mg, 5.1 mmol). The resulting reaction mixture was stirred at room temperature for 1.5 hours. Ethyl acetate was then added (200 mL) and the organic phase was washed successively with 1N HCl, saturated NaHCO3, brine, dried and evaporated. The crude product was purified by flash chromatography eluting with 25% EtOAc in hexanes to yield the title compound.

Workup

  1. customThe resulting reaction mixture
  2. washthe organic phase was washed successively with 1N HCl, saturated NaHCO3, brine
  3. customdried
  4. customevaporated
  5. customThe crude product was purified by flash chromatography
  6. washeluting with 25% EtOAc in hexanes

Sources & evidence

ORD record
ord-e051285167c6477e9c9cda9be8c9e8b3
Source dataset
uspto-grants-1992_07
Patent number
US05132319

Reaction notes

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