Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Formate | HCID 2723810 | — |
| Reactant | HCID 86642307 | HCID 86642307 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Product | HCID 86642308 | HCID 86642308 | 11% |
Reaction Steps
The mixture of allyl-(3,5-dibromo-pyrazin-2-yl)-amine (3.51 g, 12.0 mmol), TEA (4 mL, 28.8 mmol), sodium formate (204 mg, 3.00 mmol), Bu4NH4Br (580 mg, 1.80 mmol), and Pd(OAc)2 (269 mg, 1.20 mmol) in 24 mL of DMF was heated at 50° C. overnight then cooled to RT. The reaction mixture was partitioned between EtOAc and brine. The organic layer was dried (MgSO4), concentrated, and purified by SiO2 chromatography (120 g SiO2, hexanes/EtOAc 0-70% EtOAc) to give 0.279 g of 2-bromo-7-methyl-5H-pyrrolo[2,3-b]pyrazine (11% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08012974B2 |
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| Source dataset | uspto-grants-2011_09 |
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| ORD ID | ord-7c8ebd6c141746a7bef219e230228d6b |
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| Source note | uspto-grants-2011_09 |
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