HuagongsheHuagongshe Chemistry Print Report · For research reference only
Phenylacetylene → HCID 19605522, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Phenylacetylene | HCID 10821 | — |
| Reactant | 4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine | HCID 6918689 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Diethylamine | HCID 8021 | — |
| Product | HCID 19605522 | HCID 19605522 | 64.4% |
Reaction Steps
A mixture of 382 mg (1 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 112 mg (1.1 mmole) phenylacetylene, 38 mg copper(I)-iodide and 35 mg bis(triphenylphosphine)-palladium(II)-chloride in 5 ml dimethylformamide and 5 ml diethylamine is refluxed for 2 hours. The solvents are removed and the residue is diluted with dichloromethane. The dichloromethane solution is washed twice with water, dried over magnesiumsulfate and concentrated in vacuo. Recrystallisation of the residue from chloroform/ethanol yields 260 mg (64%) pure 4-(2-phenylethynyl-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine als a pale yellow solid mp.: 202-204° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05990105 |
| Source dataset | uspto-grants-1999_11 |
| ORD ID | ord-af5f623bf2494902ad7d90afdc584c4d |
| Source note | uspto-grants-1999_11 |