Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylformamide | HCID 6228 | — |
| Reactant | 3-(N-BOC-aminomethyl)-5-bromopyridine | HCID 46739290 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | HCID 178418397 | HCID 178418397 | — |
| Solvent | Diethyl Ether | HCID 3283 | — |
| Product | HCID 86647427 | HCID 86647427 | 86% |
Reaction Steps
To tert-butyl (5-bromopyridin-3-yl)methylcarbamate (384 mg, 1.34 mmol) in DMF (10 ml), Zn(CN)2 (94 mg, 0.80 mmol) and Pd(PPh3)4 were added and heated at 110° C. for 3 h. Then the reaction mixture was cooled to RT, diluted with ether, washed with ammonium hydroxide solution, water and brine. Crude residue was column chromatographed (40% ethylacetate/60% Hexanes) to yield tert-butyl (5-cyanopyridin-3-yl)methylcarbamate in 86% yield.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US08299267B2 |
|---|
| Source dataset | uspto-grants-2012_10 |
|---|
| ORD ID | ord-ae46e02925904f5d80074ae9b8aaca1b |
|---|
| Source note | uspto-grants-2012_10 |
|---|
