Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Binap, (A+-)- | HCID 634876 | — |
| Reactant | 1-(4-Amino-5-chloro-1H-pyrazol-1-yl)-2-methylpropan-2-ol | HCID 69281663 | — |
| Reactant | 6-(2-Chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole | HCID 86726420 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 86726480 | HCID 86726480 | 97% |
Reaction Steps
To a degassed mixture of 1-(4-amino-5-chloro-1H-pyrazol-1-yl)-2-methylpropan-2-ol (1 equiv), 6-(2-chloro-4-(cyclopentyloxy)-7-((2-(trimethylsilyl)ethoxy)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-2-methylbenzo[d]oxazole (1.01 equiv) and 2,2′-bis-diphenylphosphanyl-[1,1′]binaphthalenyl (0.1 equiv) in 1,4-dioxane (0.08 M) was added palladium acetate (0.1 equiv) and cesium carbonate (3 equiv). The reaction was stirred at 100° C. for 2 h. Upon completion, the reaction mixture was cooled to room temperature and concentrated to give the title compound which was used directly in next step without further purification (97% yield). MS (ESI) m/z 652.2 [M+H]+.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09428509B2 |
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| Source dataset | uspto-grants-2016_08 |
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| ORD ID | ord-1e0a8ff89e004bfd88bdd49a35dfefeb |
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| Source note | uspto-grants-2016_08 |
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