Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | HCID 22288640 | HCID 22288640 | — |
| Reactant | HCID 22288643 | HCID 22288643 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Ethanol | HCID 702 | — |
| Product | HCID 22288648 | HCID 22288648 | 73.1% |
Reaction Steps
To a toluene (80 mL) solution containing 4-{2-[(6-bromo-2-pyridinyl)oxy]ethoxy}benzaldehyde (1 g) and tetrakis(triphenylphosphine)palladium (0.18 g), a 2M aqueous solution (4 mL) of sodium carbonate and a solution of 2,4-difluorophenylbenzeneboronic acid (0.64 g) in ethanol (4 mL) were added. The resultant mixture was refluxed for four hours. After completion of reaction, the reaction mixture was poured into saturated saline, and the thus-obtained toluene layer of the resultant mixture was separated. The separated layer was dried over magnesium sulfate, and the residual solvent was removed through distillation under reduced pressure. The thus-yielded residue was purified by means of a silica gel column, to thereby yield 0.71 g of the title compound as colorless crystals (yield 64.5%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US06958353B2 |
|---|
| Source dataset | uspto-grants-2005_10 |
|---|
| ORD ID | ord-93e75e556a8e4d85a543152013c18b3c |
|---|
| Source note | uspto-grants-2005_10 |
|---|