Water → HCID 135910362, compound

HRID 2423102Notes

Reaction equation

HRID 2423102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([OH:26])[C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17]CC4C=CC=CC=4)=[C:13]([F:25])[CH:12]=3)[C:9]=2[CH:10]=1.B(Br)(Br)Br.O.C([O-])(O)=O.[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([OH:26])[C:5]2[CH:6]=[N:7][N:8]([C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[C:13]([F:25])[CH:12]=3)[C:9]=2[CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 136085248HCID 136085248, compound

Product 1

HCID 135910362HCID 135910362, compoundYield 77.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

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).

Workup

  1. temperatureit was warmed to room temperature
  2. extractionThe solution was extracted with EtOAc (2×)
  3. dry with materialthe combined organics were dried over MgSO4
  4. customThe crude material (49 mg) was then purified by flash chromatography with a gradient of 5-100% EtOAc in hexane

Sources & evidence

ORD record
ord-2e041e48bb7f4c2ba4b5bbbe97545663
Source dataset
uspto-grants-2011_06
Patent number
US07960563B2

Reaction notes

Loading…