HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Methyl-3-butyn-2-ol → HCID 19605481, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Methyl-3-butyn-2-ol | HCID 8258 | — |
| 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 19605481 | HCID 19605481 | 52% |
Reaction Steps
A mixture of 382 mg (1 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 93 mg (1.1 mmole) 2-methyl-3-butyn-2-ol, 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. Flash chromatography (silicagel, hexane/ethyl acetate 7/3 ) and recrystallisation of the residue from ethanol yields 200 mg (52%) pure 4-[4-(4-amino-benzenesulfonyl)-6-pyrrolidine-1-yl-pyridine-2-yl]-2-methyl-but-3-yn-2-ol als a white solid mp.: 168-170° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05990105 |
| Source dataset | uspto-grants-1999_11 |
| ORD ID | ord-57a54eeadcc54449942b54f0e668feca |
| Source note | uspto-grants-1999_11 |