Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | Tert-butyl [(6-chloropyridin-3-yl)methyl]carbamate | HCID 15449580 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 21904630 | HCID 21904630 | 90% |
Reaction Steps
Under a nitrogen atmosphere, add 3-(tert-butoxycarbonylamino-methyl)-6-chloropyridine (13.1 g, 54 mmol), zinc cyanide (9.5 g, 81 mmol), tris(dibenzylideneacetone)dipalladium(0) (494 mg, 0.54 mmol), and dppf (550 mg, 0.81 mmol) to DMF (130 mL). Heat the mixture at 70° C. overnight. Cool the mixture to room temperature and dilute with water and EtOAc. Separate the layers, and extract the aqueous layer with EtOAc. Wash the combined organic extracts with water and brine. Dry the organic solution over Na2SO4, filter, and concentrate in vacuo. Purify by chromatography on silica gel (500 g) eluting with hexane/EtOAc (1:0 to 7:3 gradient) to provide the desired intermediate as a white solid (11.3 g, 90%). MS (ES+) m/z: 234 (M+H)+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08680091B2 |
|---|
| Source dataset | uspto-grants-2014_03 |
|---|
| ORD ID | ord-77a29fa14eb84c5d922b3d33b491c23a |
|---|
| Source note | uspto-grants-2014_03 |
|---|
