Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Hydrochloric Acid | HCID 313 | — |
| Reactant | Nitrogen | HCID 947 | — |
| Reactant | Stannane, tributyl(1-ethoxyethenyl)- | HCID 619414 | — |
| Reactant | 2-(Di-tert-butylphosphino)biphenyl | HCID 2734215 | — |
| Reactant | HCID 67241679 | HCID 67241679 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Methanol | HCID 887 | — |
| Solvent | Water | HCID 962 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 67240477 | HCID 67240477 | — |
Reaction Steps
To a N2 flushed vial was added 5-[1-(4-chloro-2-iodo-benzyl)-1H-indazol-5-ylmethylene]-2-(4-methyl-piperazin-1-yl)thiazol-4-one (100 mg, 0.15 mmol), Pd2(dba)3 (10 mg, 0.011 mmol), biphenyl-2-yl-di-t-butyl-phosphane (12 mg, 0.04 mmol), Tributyl-(1-ethoxy-vinyl)-stannane (86 mg, 0.23 mmol) and dioxane (2 mL). The resulting mixture was heated at 90° C. for 16 h. The resulting mixture was poured into water and extracted with EtOAc. The organic layer was dried and concentrated, and the residue was purified by preparative HPLC to yield a white solid which was treated 1 N hydrochloric acid in MeOH to yield the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08263781B2 |
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| Source dataset | uspto-grants-2012_09 |
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| ORD ID | ord-6ac1fa30c91d42ff9f0cba5c9ba004cb |
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| Source note | uspto-grants-2012_09 |
|---|