Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Toluene | HCID 1140 | — |
| Reactant | 4-Bromo-3-fluorobenzotrifluoride | HCID 142414 | — |
| Reactant | Sodium t-butoxide | HCID 23676156 | — |
| Reactant | 2-(4-(Trifluoromethoxy)phenyl)-2,8-diazaspiro[4.5]decan-1-one | HCID 66742759 | — |
| Catalyst | Binap, (A+-)- | HCID 634876 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Solvent | Ethyl Acetate | HCID 8857 | — |
| Product | HCID 56655538 | HCID 56655538 | 66% |
Reaction Steps
A sealed tube was charged with 4-bromo-3-fluorobenzotrifluoride (40 mg, 0.16 mmol), 2-(4-trifluoromethoxy-phenyl)-2,8-diaza-spiro[4.5]decan-1-one (50 mg, 0.16 mmol), sodium tert-butoxide (17 mg, 0.18 mmol), tris(dibenzylidene acetone)dipalladium-(0) (15 mg, 0.02 mmol), BINAP (5 mg, 0.01 mmol) and toluene (2) under argon. The sealed tube was closed and immersed in an oil bath and heated to 80° C. for 15 h. The reaction mixture was allowed to cool to room temperature, diluted in ethyl acetate, filtered, and concentrated in vacuo to give a crude residue which was purified by flash column chromatography to yield the title compound as a light yellow solid (50 mg, 66%). MS (ESI): 477.1 (MH+)
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08552024B2 |
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| Source dataset | uspto-grants-2013_10 |
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| ORD ID | ord-74d344748a2c48e6882aff6226167989 |
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| Source note | uspto-grants-2013_10 |
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