HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 2245230Generated: October 26, 2026
4-Bromo-2-chloropyridine → Isobutyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate
https://huagongshe.com/reaction/2245230
Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 4-Bromo-2-chloropyridine | HCID 3847770 | — |
| Reactant | Isobutyl piperazine-1-carboxylate | HCID 11788701 | — |
| Reactant | sodium 2-methylpropan-2-olate | HCID 178418730 | — |
| Catalyst | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Toluene | HCID 1140 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | Isobutyl 4-(2-chloropyridin-4-yl)piperazine-1-carboxylate | HCID 58853192 | 63.1% |
Reaction Steps
4-Bromo-2-chloropyridine (125 mg, 0.65 mmol), isobutyl piperazine-1-carboxylate (93 mg, 0.5 mmol), Pd2(dba)3 (10 mg, 10 μmol), t-BuONa (72 mg, 0.75 mmol), and Xantphos (17 mg, 30 μmol) in dry toluene (5 mL) were sealed in a microwave vessel and heated by microwave irradiation at 150° C. for 15 minutes. The reaction was diluted with EtOAc, washed with water, dried over Na2SO4, and evaporated under reduced pressure. Purification by flash chromatography (SiO2, MeOH/CH2Cl2) afforded 3a as a tan oil (94 mg, 63% yield). LCMS: m/z 298.5 (M+H)+ at 1.93 minutes (10%-99% CH3CN/H2O), (10%-99% CH3CN (0.035% TFA)/H2O (0.05% TFA).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07683065B2 |
|---|
| Source dataset | uspto-grants-2010_03 |
|---|
| ORD ID | ord-167526362202448496cfb45ef8f4755c |
|---|
| Source note | uspto-grants-2010_03 |
|---|
