Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Cesium carbonate | HCID 10796 | — |
| Reactant | Benzophenone imine | HCID 136809 | — |
| Reactant | 3-Bromo-5-(trifluoromethyl)pyridine | HCID 11127991 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | 1,4-Dioxane | HCID 31275 | — |
| Product | HCID 90020550 | HCID 90020550 | 98% |
Reaction Steps
Add 3-bromo-5-(trifluoromethyl)pyridine (600 mg, 2.67 mmol), benzophenone imine (701 mg, 4.0 mmol), Cs2CO3 (2.17 g, 6.68 mmol), BINAP (25 mg, 0.040 mmol), Pd2(dba)3 (24 mg, 0.027 mmol) in 1,4-dioxane (10 mL), stir at 110° C. for 16 hrs. Cool to room temperature, add water (100 mL), extract with EtOAc (15 mL×3), wash the combined organic layers with brine, dry over anhydrous Na2SO4, concentrate under reduced pressure to give the crude product. Purification by chromatography (silica gel, EtOAc:PE=6:94) affords the target compound (850 mg, 98%).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09359338B2 |
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| Source dataset | uspto-grants-2016_06 |
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| ORD ID | ord-37b0df9789f64306950ea523754d7a57 |
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| Source note | uspto-grants-2016_06 |
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