HuagongsheHuagongshe Chemistry Print Report · For research reference only
(4-Methoxyphenyl)boronic acid → 4-[2-(4-Methoxy-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | (4-Methoxyphenyl)boronic acid | HCID 201262 | — |
| Reactant | 4-(2-Bromo-6-pyrrolidin-1-ylpyridine-4-sulfonyl)phenylamine | HCID 6918689 | — |
| Catalyst | Dichlorobis(triphenylphosphine)palladium | HCID 6102075 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Potassium Carbonate | HCID 11430 | — |
| Product | 4-[2-(4-Methoxy-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine | HCID 19605456 | 70.8% |
Reaction Steps
A mixture of 191 mg (0.5 mmole) 4-(2-bromo-6-pyrrolidine-1-yl-pyridine-4-sulfonyl)-phenylamine, 77 mg (0.55 mmole) 4-methoxyphenylboronic acid, 18 mg bis(triphenylphosphine)-palladium(II)-chloride is refluxed for 2 hours in 7 ml toluene and 2 ml 2N aqueous potassium carbonate. The solvents are removed in vacuo. Flash chromatography (Silicagel, ethyl acetate/hexane 1/1) of the residue yields 145 mg (70%) pure 4-[2-(4-methoxy-phenyl)-6-pyrrolidine-1-yl-pyridine-4-sulfonyl]-phenylamine as a pale yellow solid mp.: 227-229° C.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05990105 |
| Source dataset | uspto-grants-1999_11 |
| ORD ID | ord-6ab7c7fa596c4993a14ddd8f869cc839 |
| Source note | uspto-grants-1999_11 |