Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Sodium Cyanide | HCID 8929 | — |
| Reactant | HCID 21099423 | HCID 21099423 | — |
| Solvent | Dimethyl Sulfoxide | HCID 679 | — |
| Product | HCID 21099504 | HCID 21099504 | 36% |
Reaction Steps
2,4-Difluoro-1-(2-{4-[(4-fluorophenyl)sulfonyl]phenyl}ethyl)benzene (Example 122, 20 mg, 0.053 mmol) was dissolved in dimethylsulfoxide (0.1 mL) and sodium cyanide (5.2 mg, 0.106 mmol) was added. The reaction was heated to 100° C. overnight. The cooled reaction mixture was partitioned between ethyl acetate and water. The organic layer was dried over Na2SO4 and evaporated in vacuo. The residue was purified by flash column chromatography on silica, eluting with 25% ethyl acetate/isohexane, to yield the title compound as a white solid (7 mg, 36%) δH (400 MHz, d6 DMSO): 8.10-8.07 (4H, m), 7.89 (2H, d, J=8.4 Hz), 7.46 (2H, d, J=8.4 Hz), 7.29 (1H, q, J=7.6 Hz), 7.14-7.10 (1H, m), 6.98-6.94 (1H, m), 2.94-2.86 (4H, m).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07468393B2 |
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| Source dataset | uspto-grants-2008_12 |
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| ORD ID | ord-92552b70f0274145abb6d04dd33ab3af |
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| Source note | uspto-grants-2008_12 |
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