Participants
| Role | Name | HCID | Charge |
|---|
| Reactant | Water | HCID 962 | — |
| Reactant | Boron tribromide | HCID 25134 | — |
| Reactant | Sodium Bicarbonate | HCID 516892 | — |
| Reactant | HCID 136085248 | HCID 136085248 | — |
| Solvent | Dichloromethane | HCID 6344 | — |
| Product | HCID 135910362 | HCID 135910362 | 77.1% |
Reaction Steps
To a suspension of 6-chloro-1-{3-fluoro-4-[(phenylmethyl)oxy]phenyl}-1H-indazol-4-ol (D11) (60 mg, 0.163 mmol) in dry DCM (2 mL) cooled to −78° C. was added BBr3 (1M in DCM, 0.326 mL, 0.326 mmol) dropwise. The resulting mixture was stirred at this temperature for 1 hour, then it was warmed to room temperature, treated with water and the pH adjusted to 7 by addition of saturated NaHCO3. The solution was extracted with EtOAc (2×) and the combined organics were dried over MgSO4. The crude material (49 mg) was then purified by flash chromatography with a gradient of 5-100% EtOAc in hexane to give a the title compound (E8) as a colourless solid (35 mg).
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
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| Patent number | US07960563B2 |
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| Source dataset | uspto-grants-2011_06 |
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| ORD ID | ord-2e041e48bb7f4c2ba4b5bbbe97545663 |
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| Source note | uspto-grants-2011_06 |
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