Triethylamine → (R)-5-(2-Ethylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole

HRID 975024Notes

Reaction equation

HRID 975024 reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17].[CH:18]([S:20]([CH2:23][CH3:24])(=[O:22])=[O:21])=[CH2:19].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(#N)C>[CH2:23]([S:20]([CH:18]=[CH:19][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:11][C@H:12]1[CH2:16][CH2:15][CH2:14][N:13]1[CH3:17])(=[O:22])=[O:21])[CH3:24]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 74680(Ethylsulfonyl)etheneHCID 80271Tri-o-tolylphosphineHCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole

Product 1

HCID 54504320(R)-5-(2-Ethylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indoleYield 65.3%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of (R)-5-bromo-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole (0.25 g), ethyl vinyl sulphone (0.14 g), tri-o-tolylphosphine (0. 075 g), palladium (II) acetate (0. 013 g), triethylamine (0.25 mL) and acetonitrile (3 mL) was heated under reflux for 17 hours in an atmosphere of nitrogen. The mixture was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane/ethanol/concentrated aqueous ammonia (90:8:1) gave the title compound as a foam (0.185 g): TLC (dichloromethane/-ethanol/concentrated aqueous ammonia, 90:10:1): Rf =0.5. Anal. Calcd for C18H24N2O2S. 0.2 CH2Cl2 : C, 62.55; H, 7.04; N, 8.02. Found: C, 62.65; H, 6.94; N, 7.92.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 17 hours in an atmosphere of nitrogen
  3. customThe mixture was evaporated
  4. customthe residue was chromatographed on silica gel
  5. washElution with dichloromethane/ethanol/concentrated aqueous ammonia (90:8:1)

Sources & evidence

ORD record
ord-7976cb42440c4517bd6d1e99f4e3e773
Source dataset
uspto-grants-1997_03
Patent number
US05607951

Reaction notes

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