HuagongsheHuagongshe Chemistry Print Report · For research reference only
Sodium Carbonate → 4-(4-Bromo-3-fluorophenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 1-Bromo-2-fluoro-4-iodobenzene | HCID 2725006 | — |
| Reactant | (Pyridin-4-yl)boronic acid | HCID 2734379 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane--water (1/1) | HCID 21886435 | — |
| Product | 4-(4-Bromo-3-fluorophenyl)pyridine | HCID 66684127 | 21.9% |
Reaction Steps
1-Bromo-2-fluoro-4-iodobenzene (300 mg, 0.997 mmol), 4-pyridineboronic acid (147 mg, 1.196 mmol), Na2CO3(211 mg, 1.994 mmol) and tetrakis(triphenylphosphine)palladium (230 mg, 0.199 mmol) in 3.3 mL of 1:1 Dioxane/water were heated to 100° C. for 20 h. The reaction was slowly warmed to room temperature, diluted with water and extracted with EtOAc. The organic phase was separated, dried (Na2SO4) and evaporated to dryness, giving an oil. This material was chromatographed on silica gel, eluting with 0-10% ethyl acetate in hexanes to give 4-(4-bromo-3-fluorophenyl)pyridine (55 mg) as an off-white solid.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08575150B2 |
| Source dataset | uspto-grants-2013_11 |
| ORD ID | ord-85a9374533824e999933f3cbaee06000 |
| Source note | uspto-grants-2013_11 |