HuagongsheHuagongshe Chemistry Print Report · For research reference only
Dichloromethane → 5-Amino-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Dichloromethane | HCID 6344 | — |
| Reactant | Ethyl Acetate | HCID 8857 | — |
| Reactant | 5-Bromo-3-(4-fluorophenyl)pyrazin-2-amine | HCID 71463989 | — |
| Reactant | HCID 178418416 | HCID 178418416 | — |
| Catalyst | Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+) | HCID 178418228 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Triethylamine | HCID 8471 | — |
| Product | 5-Amino-6-(4-fluoro-phenyl)-pyrazine-2-carboxylic acid methyl ester | HCID 67504641 | — |
Reaction Steps
To a solution of 1.87 g 5-bromo-3-(4-fluoro-phenyl)-pyrazin-2-ylamine in 35 ml methanol was added 15 ml ethyl acetate, 0.260 g [1,1′-bis(diphenylphosphino)ferrocen]palladium(II)chloride 1:1 complex with dichloromethane and 1.95 ml triethylamine and the mixture was stirred at 110° C. under 70 bar carbon monoxide for 18 h. The reaction mixture was evaporated and the residue was purified by chromatography on silica gel with heptane:ethyl acetate=1:1 to yield 1.26 g of the title compound as white crystals. MS (ISP) (M+H+)=248.3.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US07629346B2 |
| Source dataset | uspto-grants-2009_12 |
| ORD ID | ord-7cf0b260aca9458588db973534923d84 |
| Source note | uspto-grants-2009_12 |