Triethylamine → (R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole hydrobromide

HRID 745012Notes

Reaction equation

HRID 745012 reaction equation
[Br:1][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].[C:18]1([S:24]([CH:27]=[CH2:28])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.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>[BrH:1].[C:18]1([S:24]([CH:27]=[CH:28][C:2]2[CH:3]=[C:4]3[C:8](=[CH:9][CH:10]=2)[NH:7][CH:6]=[C:5]3[CH2:11][C@H:12]2[CH2:16][CH2:15][CH2:14][N:13]2[CH3:17])(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 79664Phenyl vinyl sulfoneHCID 80271Tri-o-tolylphosphineHCID 11185464(R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole

Product 1

HCID 57370880(R)-5-(2-phenylsulphonylethenyl)-3-(N-methylpyrrolidine-2-yl-methyl)-1H-indole hydrobromideYield 61%

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), phenylvinylsulphone (0.19 g), tri-o-tolylphosphine (0.075 g), palladium (II) acetate (0.0125 g), triethylamine (0.25 mL) and acetonitrile (2.5 mL) was heated under reflux for 42 hours in an atmosphere of nitrogen. The solvent was evaporated and the residue was chromatographed on silica gel. Elution with dichloromethane/methanol/concentrated aqueous ammonia (90:10:1) gave the title compound as a foam (0.24 g): Anal. Calcd for C22H24N2O2S. HBr. 1/3 CH2Cl2 : C,54.77; H,5.29; N,5.72. Found: C,55.00; H,4.85; N,5.58.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 42 hours in an atmosphere of nitrogen
  3. customThe solvent was evaporated
  4. customthe residue was chromatographed on silica gel
  5. washElution with dichloromethane/methanol/concentrated aqueous ammonia (90:10:1)

Sources & evidence

ORD record
ord-107364ae0a3c4c8d87b198f3df22daa8
Source dataset
uspto-grants-1996_09
Patent number
US05559246

Reaction notes

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