Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | HCID 61286363 | HCID 61286363 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86718466 | HCID 86718466 | 73% |
Reaction Steps
A mixture of 1.2 g (4.6 mmol) of 6-chloro-3-nitro-2-(tetrahydro-pyran-4-yloxy)-pyridine, 550 mg (4.7 mmol) zinc cyanide, 260 mg (0.47 mmol) 1,1′-bis(diphenylphosphino)-ferrocene, 215 mg (0.24 mmol) Pd2dba3 in DMF are stirred at 120° C. for 5 h and 100° C. over night. After cooling to RT, the reaction mixture is diluted with EtOAc, washed with 10% aq. K2CO3 solution, water and brine, dried and evaporated. The residual is purified by FC, giving rise to 840 mg (73%) 5-Nitro-6-(tetrahydro-pyran-4-yloxy)-pyridine-2-carbonitrile.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08901138B2 |
|---|
| Source dataset | uspto-grants-2014_12 |
|---|
| ORD ID | ord-edb53ec245aa4b6db1b5401a7cac8d85 |
|---|
| Source note | uspto-grants-2014_12 |
|---|
