HuagongsheHuagongshe Chemistry Print Report · For research reference only
Acetonitrile → 1-(2-diethylamino-ethyl)-2,3-dihydro-1H-indol-5-ylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Acetonitrile | HCID 6342 | — |
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | 1-Bromo-2-chloro-4-nitrobenzene | HCID 34667 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Product | 1-(2-diethylamino-ethyl)-2,3-dihydro-1H-indol-5-ylamine | HCID 28418953 | — |
Reaction Steps
Under a nitrogen atmosphere 12.5 mL (0.090 mol) of 3-N,N-diethylamino-propyne was added to 25.00 g (0.106 mol) of 4-bromo-3-chloro-nitrobenzene, 43.7 mL (0.315 mol) of triethylamine, 10.40 g (0.009 mol) of tetrakis[triphenylphosphine]-palladium(II) and 1.71 g (0.009 mol) of copper(I)-iodide in 250 mL acetonitrile and the mixture was refluxed for 18 hours. The reaction mixture was evaporated down i. vac., combined with EtOAc and the organic phase was washed with water. The org. phase was evaporated down i. vac. and the residue was purified by column chromatography (silica gel, petroleum ether/EtOAc 10:0→4:1) followed by column chromatography (silica gel, dichloromethane).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07351719B2 |
| Source dataset | uspto-grants-2008_04 |
| ORD ID | ord-6b503742cda149c79f0bc141fe7bb514 |
| Source note | uspto-grants-2008_04 |