Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Triethylamine | HCID 8471 | — |
| Reactant | Tri-o-tolylphosphine | HCID 80271 | — |
| Reactant | 2-amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine | HCID 59262247 | — |
| Reactant | HCID 178434313 | HCID 178434313 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 178434253 | HCID 178434253 | 70.9% |
Reaction Steps
To a solution of -amino-5-bromo-3-[(S)-4-Boc-3-benzylpiperazinyl]pyrazine 108 (100 mg, 0.223 mmol) and 3-methyl-5-trimethylstannanyl-1H-indazole 105 (66 mg, 0.223 mmol.) in DMF (3.5 mL) was added tris(dibenzylideneacetone)bipalladium (10 mg, 0.011 mmol), tri-o-tolylphosphine (7 mg, 0.023 mmol) and triethylamine (23 mg, 0.23 mmol). The reaction mixture was heated in a microwave reactor at 120° C. for 10 minutes. Ethyl acetate (100 mL) was added. The organic layer was washed with water and brine. The organic layer was dried over sodium sulfate and filtered through Celite. The organic solvent was evaporated under reduced pressure. The crude product was purified by RP-HPLC to yield the desired 2-amino-3-[(S)-4-Boc-3-benzylpiperazinyl]-5-(3-methyl-1H-indazol-5-yl)pyrazine 109 (79 mg, 0.158 mmol).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07700601B2 |
|---|
| Source dataset | uspto-grants-2010_04 |
|---|
| ORD ID | ord-bae172de31624776a06f45ae5abb7fdb |
|---|
| Source note | uspto-grants-2010_04 |
|---|