HuagongsheHuagongshe Chemistry Print Report · For research reference only
Tetrahydrofuran → Methyl 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenyl)-3-oxo-2,3-dihydrofuro[2,3-b]pyridine-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Tetrahydrofuran | HCID 8028 | — |
| Reactant | Lithim bis(trimethylsilylamide) | HCID 86588160 | — |
| Reactant | Methyl {[5-(4-chlorophenyl)-3-cyano-6-(2,4-dichlorophenyl)pyridin-2-yl]oxy}(3,4-difluorophenyl)acetate | HCID 86602010 | — |
| Product | Methyl 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenyl)-3-oxo-2,3-dihydrofuro[2,3-b]pyridine-2-carboxylate | HCID 21984819 | — |
Reaction Steps
To a magnetically stirred solution of 1.20 g (2.14 mmol) the product of Step A dissolved in 12 mL of THF was slowly added 3.2 mL of a 1.0 N solution (3.2 mmol) of lithium bis(trimethylsilylamide) in THF at 0° C. The reaction mixture was stirred for 30 min and allowed to warm to room temperature. The reaction mixture was then quenched by addition of excesss 10% aqueous NaHSO4 and extracted into EtOAc. The organic layer was separated, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with chloroform. Combination of the purified fractions and drying in vacuo afforded the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07091216B2 |
| Source dataset | uspto-grants-2006_08 |
| ORD ID | ord-56f0e6a441a9460baf2227bb5042856e |
| Source note | uspto-grants-2006_08 |