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

HRID 744153Notes

Reaction equation

HRID 744153 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-2ylmethyl)-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-02539d359e334e8fb7a27b8ff9c06540
Source dataset
uspto-grants-1996_09
Patent number
US05559129

Reaction notes

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