HuagongsheHuagongshe Chemistry Print Report · For research reference only
2-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridine → 2-(tert-Butyldiphenylsiloxy)methyl-6-(4-fluorophenyl)pyridine
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | 2-Bromo-6-(tert-butyldiphenylsiloxy)methylpyridine | HCID 23370237 | — |
| Reactant | HCID 178418676 | HCID 178418676 | — |
| Catalyst | Tetrakis(triphenylphosphine)palladium | HCID 11979704 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Solvent | Tetrahydrofuran | HCID 8028 | — |
| Product | 2-(tert-Butyldiphenylsiloxy)methyl-6-(4-fluorophenyl)pyridine | HCID 23370183 | — |
Reaction Steps
A mixture of 2-bromo-6-(tert-butyldiphenylsiloxy)methylpyridine (1 g; WO 94/00444), 4-fluorophenylmagnesium bromide (3.5 mL of a 2M solution in Et2O) and tetrakis (triphenylphosphine) palladium (200 mg) in THF (20 mL) was refluxed for 4 h. To the mixture was added NH4OAc buffer and the mixture was extracted with EtOAc. The organics were dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc (30:1)) to provide the title compound as an oil.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US05576338 |
| Source dataset | uspto-grants-1996_11 |
| ORD ID | ord-79187af6a1a34680acdd1d53a5bf3975 |
| Source note | uspto-grants-1996_11 |