Potassium Carbonate → (R)-7-benzyloxy-3-(2-phthalimidopropyl)indole

HRID 1241229Notes

Reaction equation

HRID 1241229 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32])[CH2:20]I)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].C([O-])=O.[NH4+]>[Pd].CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:17]=1[NH:16][CH:15]=[C:14]2[CH2:18][C@H:19]([N:22]1[C:23](=[O:32])[C:24]2=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]2[C:26]1=[O:27])[CH3:20])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2723923Ammonium formateHCID 58713923(S)-7-benzyloxy-3-(3-iodo-2-phthalimidopropyl)indole

Product 1

HCID 58713922(R)-7-benzyloxy-3-(2-phthalimidopropyl)indoleYield 79.4%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
85 °C

Procedure

A 10% palladium on carbon catalyst (content 50%) 4.00 g was suspended in 200 ml of DMF, and 20.00 g of (S)-7-benzyloxy-3-(3-iodo-2-phthalimidopropyl)indole was added thereto. Added while stirring were 8.00 g of potassium carbonate and 6.00 g of ammonium formate, the suspension was heated in an oil bath of 85° C. For one hour. After cooling down, the catalyst was filtered off, and the filtrate was diluted with ethyl acetate. Then, water was added thereto, and the organic layer was separated. The organic layer was washed in order with a 10% sodium thiosulfate aqueous solution, a sodium hydroxide aqueous solution, hydrochloric acid and a saturated sodium chloride aqueous solution, and then it was dried, filtered and concentrated under reduced pressure, whereby 12.16 g of the title compound was obtained in the form of a yellow amorphous solid shaped substance.

Workup

  1. additionAdded
  2. temperatureAfter cooling down
  3. filtrationthe catalyst was filtered off
  4. additionthe filtrate was diluted with ethyl acetate
  5. additionThen, water was added
  6. customthe organic layer was separated
  7. washThe organic layer was washed in order with a 10% sodium thiosulfate aqueous solution
  8. dry with materiala sodium hydroxide aqueous solution, hydrochloric acid and a saturated sodium chloride aqueous solution, and then it was dried
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-50f534378dfb43568c08aa0ecd0fbed0
Source dataset
uspto-grants-2006_10
Patent number
US07115412B2

Reaction notes

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