Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | (R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole | HCID 11185464 | — |
| Reactant | HCID 22502783 | HCID 22502783 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 9842227 | HCID 9842227 | — |
Reaction Steps
A mixture of 4-methylsulphonylphenyltri-n-butylstannane (see Preparation 15) (680 mg, 1.53 mmol) tri-o-tolyphosphine (120 mg, 0,394 mmol), palladium (II) acetate (15 mg, 0.067 mmol), triethylamine (0.40 ml, 2.87 mmol) and 5-bromo-3-(1-methylpyrrolidin-2(R)-ylmethyl)-1H-indole (400 mg, 1.36 mmol) (see Preparation 36) in anhydrous acetonitrile (5 ml) was heated under reflux, under nitrogen, for 18 hours. The reaction mixture was then evaporated under reduced pressure and dichloromethane (25 ml) was added. The resultant solution was washed with aqueous sodium carbonate, dried (Na2SO4) and evaporated. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate/diethylamine (98:2) to afford, after combination and evaporation of the appropriate fractions, the title compound as a white foam, (189 mg). Found: C,68.17; H,6.81; N,7.53; C21H24N2O2S.1/20 CH2Cl2 requires: C,67.83; H,6.51; N,7.52%.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US05502065 |
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| Source dataset | uspto-grants-1996_03 |
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| ORD ID | ord-37a6feab69b84ce99f1fe057cbd60b83 |
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| Source note | uspto-grants-1996_03 |
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