HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → HCID 86634552, compound
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Sodium Carbonate | HCID 10340 | — |
| Reactant | Bis(pinacolato)diborane | HCID 2733548 | — |
| Reactant | 5-bromo-2,4-difluoro-N-(4-hydroxy-cyclohexyl)-benzenesulfonamide | HCID 68629653 | — |
| Reactant | HCID 86634551 | HCID 86634551 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | 1,2-Dimethoxyethane | HCID 8071 | — |
| Product | HCID 86634552 | HCID 86634552 | — |
Reaction Steps
A suspension of 5-bromo-2,4-difluoro-N-(4-hydroxy-cyclohexyl)-benzenesulfonamide-intermediate DX (300 mg, 0.81 mmol), BIS(pinacolato)diboron (222 mg, 0.88 mmol) and Pd(dppf)Cl2.DCM (0.066 g, 0.08 mmol) in DME (12 ml) is heated at reflux for 4 hours. 2M Na2CO3 (4 ml) is added to the reaction mixture followed by 3-amino-6-bromo-pyrazine-2-carboxylic acid methoxy-methyl-amide (0.211 g, 0.81 mmol) and Pd(dppf)Cl2.DCM (0.066 g, 0.08 mmol). The reaction mixture is refluxed for 30 minutes. The crude reaction mixture is purified by normal phase chromatography (30-100% EtOAc/iso-hexane) to afford a white solid as the titled compound. [M+H]+ 472
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US08268834B2 |
| Source dataset | uspto-grants-2012_09 |
| ORD ID | ord-167d8b3514244d87bef80cecb6de6f72 |
| Source note | uspto-grants-2012_09 |