HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 3-Bromo-5-(3-methoxyphenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | 3,5-Dibromopyridine | HCID 69369 | — |
| Reactant | (3-Methoxyphenyl)boronic acid | HCID 2734370 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Solvent | Sodium Carbonate | HCID 10340 | — |
| Product | 3-Bromo-5-(3-methoxyphenyl)pyridine | HCID 52937144 | — |
Reaction Steps
A solution of 3-methoxy-phenylboronic acid (1.0 eq, 300 mg, 1.27 mmol) in DME (3 ml) and 2M sodium carbonate solution (1.2 ml) under an inert atmosphere of argon is treated with 3,5-dibromopyridine (300 mg, 1.27 mmol) followed by PdCl2(dppf).DCM (0.1 eq, 93 mg) and then is heated using microwave radiation at 90° C. for 30 minutes. The mixture is extracted with DCM and the organic extracts are washed with water. The solvent is removed in vacuo and the crude product is purified by chromatography on silica eluting with 0-30% EtOAc in iso-hexane to afford the title compound [M+H]+=265.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431578B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-39bc28ca1f7d4ad38c1a7c71ce2165dd |
| Source note | uspto-grants-2013_04 |