HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → (4-(5-Bromopyridin-3-yl)phenyl)-(4-isopropylpiperazin-1-yl)-methanone
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | 3,5-Dibromopyridine | HCID 69369 | — |
| Reactant | (4-Isopropyl-piperazin-1-yl)-[4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-phenyl]-methanone | HCID 68756040 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | (4-(5-Bromopyridin-3-yl)phenyl)-(4-isopropylpiperazin-1-yl)-methanone | HCID 68733155 | — |
Reaction Steps
A solution of (4-isopropylpiperazin-1-yl)-(4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl) phenyl)-methanone (step 1) (1.0 eq, 778 mg) in DME (4 ml) and 2M sodium carbonate solution (2 eq, 2.2 ml) is treated with 3,5-dibromopyridine (1 eq, 514 mg) followed by PdCl2(dppf).DCM (0.1 eq, 159 mg). The resulting mixture is heated using microwave radiation at 90° C. for 1 h. The mixture is extracted with DCM and the organic extracts are washed with water. The solvent is removed in vacuo and the crude product is purified by chromatography on silica eluting with 0-100% EtOAc in iso-hexane followed by 0-5% MeOH in DCM to afford the title compound [M+H]+=388/390.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08431578B2 |
| Source dataset | uspto-grants-2013_04 |
| ORD ID | ord-9f6f8b2af2c549b0a2f40c293c5ce09c |
| Source note | uspto-grants-2013_04 |