HCID 67345844, compound → HCID 67344890, compound

HRID 1669469Notes

Reaction equation

HRID 1669469 reaction equation
[CH2:1]([C:4]1[C:5]([OH:29])=[C:6]([C:10]2[NH:11][C:12]3[C:17]([C:18]=2[CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)=[CH:16][CH:15]=[C:14]([C:25]([O:27][CH3:28])=[O:26])[CH:13]=3)[CH:7]=[CH:8][CH:9]=1)[CH:2]=[CH2:3]>CCOC(C)=O.[Pd]>[CH:19]1([C:18]2[C:17]3[C:12](=[CH:13][C:14]([C:25]([O:27][CH3:28])=[O:26])=[CH:15][CH:16]=3)[NH:11][C:10]=2[C:6]2[CH:7]=[CH:8][CH:9]=[C:4]([CH2:1][CH2:2][CH3:3])[C:5]=2[OH:29])[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]1

Participants

4

Reactant 1

HCID 67345844HCID 67345844, compound

Product 1

HCID 67344890HCID 67344890, compoundYield 98%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl 2-(3-allyl-2-hydroxyphenyl)-3-cyclohexyl-1H-indole-6-carboxylate was dissolved in EtOAc (0.08M). After adding Pd/C (10%) HOAc was added and the mixture was degassed and flushed with Ar. After degassing, H2-atmosphere was applied and the mixture was left stirring at RT. After 30 min the reaction was complete and the catalyst was filtered off. After evaporation of the solvents the product was obtained as a yellowish solid (98%). (ES+) m/z 392 (M+H)+.

Workup

  1. additionwas added
  2. customthe mixture was degassed
  3. customflushed with Ar
  4. customAfter degassing
  5. waitthe mixture was left
  6. filtrationthe catalyst was filtered off
  7. customAfter evaporation of the solvents the product

Sources & evidence

ORD record
ord-1e8bb1c805ac45d2acb29f359231d252
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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