HCID 15870568, compound → HCID 15870567, compound

HRID 610058Notes

Reaction equation

HRID 610058 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)=[CH2:2]>C(OCC)(=O)C.[Pd]>[CH2:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:12][CH2:13][N:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1)[CH3:2]

Participants

4

Reactant 1

HCID 15870568HCID 15870568, compound

Product 1

HCID 15870567HCID 15870567, compoundYield 56.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

5-Vinyl-3-(2-pyrrolidinylethyl)-1H-indole (Example 10c, 8.0 mg, 0.033 mmol) in ethyl acetate (3 mL) containing a spatula tip of Pd/C (10%) was stirred at room temperature under an atmosphere of hydrogen for 2.5 h. Filtration through celite using 10% 2M methanolic ammonia in dichloromethane and evaporation of the solvent in vacuo. A final filtration through silica gel using 10% 2M methanolic ammonia in dichloromethane yielded 5-ethyl-3-(2-pyrrolidinylethyl) -1H-indole (4.5 mg, 56%).

Workup

  1. filtrationFiltration through celite
  2. custom10% 2M methanolic ammonia in dichloromethane and evaporation of the solvent in vacuo
  3. filtrationA final filtration through silica gel using 10% 2M methanolic ammonia in dichloromethane

Sources & evidence

ORD record
ord-36032e95aed24c229188d11cbd9da293
Source dataset
uspto-grants-1999_12
Patent number
US05998462

Reaction notes

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