Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 60150942 | HCID 60150942 | — |
| Reactant | HCID 66678559 | HCID 66678559 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 68295583 | HCID 68295583 | 84% |
Reaction Steps
To a solution of 9-amino-N-(2,6-diethylphenyl)-1-methyl-1,4,5,6-tetrahydropyrazolo[4′,3′:6,7]cyclohepta[1,2-d]pyrimidine-3-carboxamide (0.375 mg, 0.96 mmol) in dioxane (10 mL), tert-butyl 4-iodo-3-methoxybenzoate (0.320 mg, 0.96 mmol) and Cs2CO3 (0.470 g, 1.44 mmol) were added and the flask was evacuated and backfilled with argon. Pd2(dba)3 (0.088 g, 0.096 mmol) and Xantphos (0.110 g, 0.192 mmol) were then charged and the mixture was refluxed under argon for 4 h. After cooling to room temperature, the reaction mixture was concentrated, suspended in water (50 mL) and extracted with AcOEt. The organic phase was anidrified on Na2SO4, filtered and evaporated to dryness, the crude solid was purified by flash chromatography on silica gel (eluant: hexane/AcOEt 8/2) to afford 0.480 g (84% yield) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08916577B2 |
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| Source dataset | uspto-grants-2014_12 |
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| ORD ID | ord-1136ceb0a8cc4f418479cd91dacbe8d3 |
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| Source note | uspto-grants-2014_12 |
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