Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Ammonium Chloride | HCID 25517 | — |
| Reactant | Lithium Chloride | HCID 433294 | — |
| Reactant | cis-1-Ethoxy-2-(tri-n-butylstannyl)ethylene | HCID 5706773 | — |
| Reactant | Methyl 3-amino-5-chloropyrazine-2-carboxylate | HCID 53417426 | — |
| Catalyst | HCID 178418476 | HCID 178418476 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 71271064 | HCID 71271064 | 82.4% |
Reaction Steps
A mixture of 3-amino-5-chloro-pyrazine-2-carboxylic acid methyl ester [28643-16-5] (2 g, 10.66 mmol), lithium chloride (1.582 g, 37.3 mmol), Pd(PPh3)2Cl2 (0.748 g, 1.066 mmol) and tributyl-((Z)-2-ethoxy-vinyl)-stannane (6.42 ml, 19.19 mmol) in DMF (104 ml) under argon was heated at 80° C. bath temperature for 1.5 h. A saturated. aq. NH4Cl was added and the mixture was extracted with MTBE, then once with EtOAc/THF 3/1. The combined organic layer was washed with brine, dried with Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (cyclohexane to cyclohexane/EtOAc 1:9) to provide the title compound as yellow oil (1.96 g).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09163011B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-819a9b1a547d4468bb9fe818fd8351be |
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| Source note | uspto-grants-2015_10 |
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