HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 5-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | p-Chlorophenylboric acid | HCID 17810664 | — |
| Reactant | 5-Bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine | HCID 69071391 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | 5-(4-Chloro-phenyl)-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine | HCID 9978377 | — |
Reaction Conditions
| Temperature | 100 °C |
|---|
Reaction Steps
A mixture of 100 mg (0.27 mmol) 5-bromo-2-[4-(4-pyrrolidin-1-ylmethyl-phenyl)-but-1-ynyl]-pyridine, 85 mg (0.54 mmol) 4-chloro-phenylboric acid, 15.7 mg (0.014 mmol) tetrakis-triphenylphosphane-palladium, 0.28 mL of a 2 M aqueous Na2CO3 solution in 10 mL 1,4-dioxane is heated for 8 h at 100° C. under an argon atmosphere. The solvent is distilled off i.vac., the residue is taken up in water, exhaustively extracted with EtOAc and dried over Na2SO4. After the desiccant and solvent have been eliminated the residue is purified over neutral Alox (ICN Alumina N+5% H2O; cyc/EtOAc 7:3). The product fractions are evaporated down, the residue is triturated with PE and suction filtered.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08618132B2 |
| Source dataset | uspto-grants-2013_12 |
| ORD ID | ord-a3a109de35a44f07b79f23a3caddfcf8 |
| Source note | uspto-grants-2013_12 |