HuagongsheHuagongshe Chemistry Print Report · For research reference only
3,3-Dimethyl-1-butyne → 4-[2-(3,3-Dimethyl-but-1-ynyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 3,3-Dimethyl-1-butyne | HCID 13512 | — |
| 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 | 4-[2-(3,3-Dimethyl-but-1-ynyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine | HCID 19605508 | 65.2% |
Reaction Steps
A mixture of 382 mg (1 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 91 mg (1.1 mmole) 3,3-dimethyl-1-butyne, 38 mg copper(I)-iodide and 35 mg bis(triphenylphosphine)-palladium(II)-chloride is refluxed for 1 hour in 5 ml dimethylformamide and 5 ml diethylamine. 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 ethanol yields 250 mg (65%) pure 4-[2-(3,3-dimethyl-but-1-ynyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine als a light brown solid mp.: 242-244° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05990105 |
| Source dataset | uspto-grants-1999_11 |
| ORD ID | ord-ba8ddb6b9a0049ed9069eaa8d8b22058 |
| Source note | uspto-grants-1999_11 |