Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium fluoride | HCID 25953 | — |
| Reactant | 3-bromo-5-nitro-1-trityl-1H-indazole | HCID 58946443 | — |
| Reactant | 2-(1-Methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine | HCID 86630181 | — |
| Catalyst | Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI) | HCID 24350 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Dimethylformamide | HCID 6228 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 86630183 | HCID 86630183 | — |
Reaction Steps
2-(1-methoxy-1-methyl-ethyl)-4-tributylstannanyl-pyridine 13AO (0.1 g, 0.24 mmol), 3-bromo-5-nitro-1-trityl-1H-indazole 1AJ (0.12 g, 0.24 mmol), CsF (0.08 g, 0.53 mmol), [Pd2(dba)3] (5 mg, 0.005 mmol), Pd[P(t-Bu)3)2, and CuI (4 mg, 0.024 mmol) in DMF (2 ml) was degassed for 5 minutes. Then it was heated at 120° C. for two hours. Cooled to room temperature and diluted with EtOAc (10 ml). It was then filtered on a celite pad. Filtrate was washed with water (3 ml) and the organic extracts were dried over MgSO4. It was filtered again on a celite pad and concentrated. The residue was purified on silica gel eluting with 1/3 EtOAc/Hexane to give the desired product 3-[2-(1-methoxy-1-methyl-ethyl)-pyridin-4-yl]-5-nitro-1-trityl-1H-indazole 14AO (0.05 g, 39%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08546404B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-27e4443fef8149b6805da2aa02726018 |
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| Source note | uspto-grants-2013_10 |
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