Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | 2-Bromo-4-nitrotoluene | HCID 82189 | — |
| Reactant | 1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) | HCID 636044 | — |
| Reactant | HCID 89699616 | HCID 89699616 | — |
| Catalyst | palladium(II) acetate | HCID 167845 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 89699819 | HCID 89699819 | — |
Reaction Steps
980 mg (2.64 mmol) of the compound of Example 3A and 627 mg (2.90 mmol) of 2-bromo-4-nitrotoluene were dissolved in 13 ml of dioxane, the mixture was degassed with argon and 59 mg (0.26 mmol) of palladium(II) acetate, 229 mg (0.40 mmol) of xantphos [4,5-bis(diphenylphosphino)-9,9-dimethylxanthene] and 2.57 g (7.91 mmol) of caesium carbonate were added. The mixture was heated in a microwave oven (Biotage Initiator, with Dynamic Field Tuning) at 150° C. for 30 min. The reaction was then filtered through kieselguhr, the filtrate was concentrated under reduced pressure and the residue was subjected to flash chromatography on silica gel (mobile phase dichloromethane/ethyl acetate 2:1). This gave 980 mg (73% of theory) of the title compound.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09394309B2 |
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| Source dataset | uspto-grants-2016_07 |
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| ORD ID | ord-7ebd227208dc4c63a8b1dddc4f1147b6 |
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| Source note | uspto-grants-2016_07 |
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