HuagongsheHuagongshe Chemistry Print Report · For research reference only
Cesium carbonate → Methyl 5-(3,3-difluoroazetidin-1-yl)-6-(2-fluoroethoxyl)pyridine-2-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 3,3-Difluoroazetidine hydrochloride | HCID 2758247 | — |
| Reactant | Methyl 5-bromo-6-(2-fluoroethoxyl)pyridine-2-carboxylate | HCID 90203715 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Product | Methyl 5-(3,3-difluoroazetidin-1-yl)-6-(2-fluoroethoxyl)pyridine-2-carboxylate | HCID 90203373 | 54% |
Reaction Steps
In analogy to the procedure described in Example 1 a), methyl 5-bromo-6-(2-fluoroethoxyl)pyridine-2-carboxylate (Example 147 a, 130 mg, 467 μmol) was reacted with 3,3-difluoroazetidine hydrochloride (CAN 288315-03-7, 66.6 mg, 514 μmol) in the presence of palladium (II) acetate, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl and cesium carbonate to give the title compound (73 mg, 54%) as light yellow solid, MS (ESI) m/e=291.1 [MH+].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09303012B2 |
| Source dataset | uspto-grants-2016_04 |
| ORD ID | ord-6b756355f19544089354ff4378501184 |
| Source note | uspto-grants-2016_04 |