Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | 2-Aminopyridine | HCID 10439 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 68856796 | HCID 68856796 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Acetonitrile | HCID 6342 | — |
| Product | HCID 68905611 | HCID 68905611 | 33% |
Reaction Steps
A microwave tube is charged with [4-(6-bromobenzo[b]thiophen-2-yl)-5-chloropyrimidin-2-yl]-[3-(4-methylpiperazin-1-yl)-propyl]-amine (45 mg, 0.094 mmol), 2.5 equivalent of pyridin-2-amine (28 mg, 0.30 mmol), 2 mol % of tris(dibenzylideneacetone)dipalladium(0) (1.7 mg, 0.0020 mmol), 6 mol % of Xantphos (3.5 mg, 0.0060 mmol), 2.5 equivalent of cesium carbonate (77 mg, 0.24 mmol) and acetonitrile (2 mL). The reaction is sealed and heated under microwave condition at 150° C. for 15 minutes, cooled down, filtered and then evaporated to furnish a red oil. The crude material is subjected to reverse phase purification, eluting with 10-70% CH3CN/0.01 M NH4HCO3 in water using a C18 Xterra column, to give the title compound as a pale yellow solid (15 mg, 33% yield). ES+(m/z) 494 (35Cl) and 496 (37Cl) [M+H].
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| Patent number | US07547691B2 |
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| Source dataset | uspto-grants-2009_06 |
|---|
| ORD ID | ord-e1e89e72385447ebb93c958f10f2831b |
|---|
| Source note | uspto-grants-2009_06 |
|---|
