Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | HCID 71294052 | HCID 71294052 | — |
| Catalyst | Zinc cyanide (Zn(CN)2) | HCID 11186 | — |
| Catalyst | Zinc | HCID 23994 | — |
| Catalyst | Ferrocene-1,1'-bis-(diphenylphosphine) | HCID 635956 | — |
| Catalyst | Bis(dibenzylideneacetone)palladium | HCID 9811564 | — |
| Product | HCID 54596679 | HCID 54596679 | 42% |
Reaction Steps
Compound 77 (41.0 mg, 0.074 mmol) obtained in Example 74 was dissolved in DMA (1.60 mL). To the solution were added zinc cyanide (21.8 mg, 1.11 mmol), zinc (1.17 mg, 0.018 mmol), tris(dibenzylideneacetone)dipalladium (2.72 mg, 0.003 mmol) and 1,1′-bis(diphenylphosphino)ferrocene (2.67 mg, 0.005 mmol), and the mixture was stirred at 120° C. for 1 hour. Water was added to the reaction mixture and the mixture was filtered through Celite. The filtrate was extracted with ethyl acetate. Washing with saturated brine and drying over anhydrous magnesium sulfate were performed. After filtration, the solvent in the filtrate was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate=1/0 to 2/3) to give Compound 78 (14.0 mg, 42% yield).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US09150569B2 |
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| Source dataset | uspto-grants-2015_10 |
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| ORD ID | ord-c0abb16aa0eb4e0391ab50a6e6306350 |
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| Source note | uspto-grants-2015_10 |
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