Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Butyl bromide | HCID 8002 | — |
| Reactant | Potassium tert-butoxide | HCID 23665647 | — |
| Reactant | HCID 59547885 | HCID 59547885 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 59547836 | HCID 59547836 | 27.8% |
Reaction Steps
To a solution of N-{1-[(2-chloro-5-hydroxyphenyl)methyl]-1H-pyrazol-3-yl}-2,6-difluorobenzamide(for as preparation see Intermediate 13) (35 mg, 0.096 mmol) in DMSO (0.5 ml) was added potassium t-butoxide (10.80 mg, 0.096 mmol). The reaction was stirred for 5 min before adding 1-bromobutane (0.012 ml, 0.115 mmol, Acros). The reaction mixture was stirred under nitrogen for 72 h at ambient temperature. The reaction mixture was filtered through a hydrophobic frit and the filtrate diluted with methanol (0.5 ml) and the sample purified by MDAP on Sunfire C18 column using Acetonitrile-Water with a Formic acid modifier (Method B). The solvent was evaporated in vacuo to give the title compound as a brown gum (11.2 mg); LCMS: (System 4) MH+=420, tRET=3.41 min.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US08399436B2 |
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| Source dataset | uspto-grants-2013_03 |
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| ORD ID | ord-7fd6264158af42beb4f8b0910d400456 |
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| Source note | uspto-grants-2013_03 |
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