Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Dimethylacetamide | HCID 31374 | — |
| Reactant | HCID 67778665 | HCID 67778665 | — |
| 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 67777609 | HCID 67777609 | — |
Reaction Steps
A mixture of N-[(1S)-2-{4-[7-bromo-6-(cyclopropylmethoxy)-2H-indazol-2-yl]phenoxy}-1-methylethyl]acetamide (150 mg), tris(dibenzylideneacetone)dipalladium(0) (45 mg), 1,1′-bis(diphenylphosphino)ferrocene (54.4 mg), zinc cyanide (57.7 mg), zinc powder (10.7 mg) and N,N-dimethylacetamide (3 mL) was stirred at 120° C. for 1.5 hr under an argon atmosphere. The reaction mixture was filtered through silica gel, and the filtrate was concentrated under reduced pressure. To the residue was added water, and the mixture was extracted with ethyl acetate. The combined organic layer was washed three times with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as colorless crystals (54.5 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08729102B2 |
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| Source dataset | uspto-grants-2014_05 |
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| ORD ID | ord-640264467cb24e03803387dfb383a40d |
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| Source note | uspto-grants-2014_05 |
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