HuagongsheHuagongshe Chemistry Print Report · For research reference only
tert-Butyl piperazine-1-carboxylate → Tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | tert-Butyl piperazine-1-carboxylate | HCID 143452 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | 2-Bromo-5-iodopyridine | HCID 4738271 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate | HCID 11530243 | — |
Reaction Steps
2-bromo-5-iodopyridine (3.00 g, 10.6 mmol), tert-butyl piperazine-1-carboxylate (1.71 g, 9.2 mmol), Pd2(dba)3 (337 mg, 0.368 mmol), and XantPhos (640 mg, 1.1 mmol) were taken up in PhCH3 (90 mL). The resulting mixture was stirred 24 h at r.t. and was diluted with EtOAc (100 mL) and water (150 mL). The phases were separated, and the organic phase was dried over Na2SO4, filtered, and concentrated to afford a crude residue that was purified by silica gel chromatography to provide tert-butyl 4-(6-bromopyridin-3-yl)piperazine-1-carboxylate (4.01). LCMS-ESI+ (m/z): [M+H]+ calcd for C14H21BrN3O2: 342.08; found: 342.15.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US09376441B2 |
| Source dataset | uspto-grants-2016_06 |
| ORD ID | ord-f62ab1c80f134cffbc75afe6080e8c15 |
| Source note | uspto-grants-2016_06 |