HuagongsheHuagongshe Chemistry Print Report · For research reference only
Potassium Carbonate → 2-Chloro-4-(2-methoxyphenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Potassium Carbonate | HCID 11430 | — |
| Reactant | 2-Methoxyphenylboronic acid | HCID 2733958 | — |
| Reactant | 4-Bromo-2-chloropyridine | HCID 3847770 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Solvent | Water 1,2-dimethoxyethane | HCID 18180031 | — |
| Product | 2-Chloro-4-(2-methoxyphenyl)pyridine | HCID 58432611 | 52.5% |
Reaction Steps
To a solution of 4-bromo-2-chloro-pyridine (1.0 g, 5.2 mmol) in DME/water 10:1 (15 mL) was added (2-methoxyphenyl)boronic acid (0.79 g, 5.2 mmol), Pd(PPh3)2Cl2 (240 mg, 0.34 mmol), and K2CO3 (1.8 g, 13.0 mmol). The mixture was heated with reflux for 6 hours. It was diluted with DCM, washed three times with water, dried over MgSO4, and concentrated under reduced pressure. The residue was purified by flash chromatography (silica gel, DCM/MeOH 100:0 to 90:10) to give the title compound A1 (0.6 g, 52%). MS (ES) C12H10ClNO requires: 219. found: 220 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09242937B2 |
| Source dataset | uspto-grants-2016_01 |
| ORD ID | ord-9a43003296804426ac74d861833e89ec |
| Source note | uspto-grants-2016_01 |