HCID 53669898, compound → HCID 21195973, compound

HRID 1066801Notes

Reaction equation

HRID 1066801 reaction equation
[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:23])[C:10]3[C:15]([C:16]=2[CH:17]=[CH:18][C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1>[Pd].CN(C)C=O>[Cl:1][C:2]1[CH:25]=[CH:24][C:5]([O:6][CH2:7][C:8]2[N:9]([CH3:23])[C:10]3[C:15]([C:16]=2[CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:4][CH:3]=1

Participants

4

Reactant 1

HCID 53669898HCID 53669898, compound

Product 1

HCID 21195973HCID 21195973, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

A round bottom flask was charged with 10% palladium on activated carbon (0.150 g), 20 ml of N,N-dimethylformamide and 2-[(4-chlorophenoxy)methyl]-1-methyl-3-[2-(methoxycarbonyl)ethenyl]-1H-indole (1.44 g, 4.22 mmol). The reaction vessel was then placed under a hydrogen atomsphere for two hours. The reaction mixture was then passed through a CELITE™ pad and then partitioned between water and methylene chloride. The aqueous fraction was extracted twice with methylene chloride. The organic fractions were combined, washed with water and then brine, and dried over sodium sulfate. The solvents were removed in vacuo. The desired title product was further purified by chromatography.

Workup

  1. custompartitioned between water and methylene chloride
  2. extractionThe aqueous fraction was extracted twice with methylene chloride
  3. washwashed with water
  4. dry with materialbrine, and dried over sodium sulfate
  5. customThe solvents were removed in vacuo
  6. customThe desired title product was further purified by chromatography

Sources & evidence

ORD record
ord-648b64b4cec34a84b9fdb854fc5f45f8
Source dataset
uspto-grants-2001_06
Patent number
US06245761B1

Reaction notes

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