HuagongsheHuagongshe Chemistry Print Report · For research reference only
Triethylamine → (R)-5-(2-Ethylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | (Ethylsulfonyl)ethene | HCID 74680 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | (R)-5-Bromo-3-(1-methyl-2-pyrrolidinyl methyl)-1H-indole | HCID 11185464 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | (R)-5-(2-Ethylsulphonylethenyl)-3-(N-methylpyrrolidin-2-ylmethyl)-1H-indole | HCID 54504320 | 65.3% |
Reaction Steps
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.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05578612 |
| Source dataset | uspto-grants-1996_11 |
| ORD ID | ord-487e6668d6f6477e945bc3c6ae725c88 |
| Source note | uspto-grants-1996_11 |