Sodium Sulfate → HCID 22260811, compound

HRID 1983476Notes

Reaction equation

HRID 1983476 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([C:17](OC)=[O:18])[CH:15]=3)[N:10]([C:21]([C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].S([O-])([O-])(=O)=O.[Na+].[Na+]>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17][OH:18])[CH:15]=3)[N:10]([C:21]([C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)([C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)[C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 22260753HCID 22260753, compound

Product 1

HCID 22260811HCID 22260811, compoundYield 92.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling, a solution of 3.85 g of methyl 3-(3-fluorophenyl)-1-trityl-1H-5-indazolecarboxylate in 40 ml tetrahydrofuran was added 535 mg of lithium aluminium hydride, and the mixture was stirred at the same temperature for 5 minutes and at room temperature for further 30 minutes. The reaction mixture was ice-cooled, saturated aqueous sodium sulfate solution was added, aluminium hydroxide was precipitated, and the organic layer was decanted. To the residue was added 20 ml of tetrahydrofuran, stirred, and the organic layer was re-decanted twice. The solvent was evaporated from the collected organic layers. The residue was dissolved in 80 ml of ethyl acetate, and then the mixture was sequentially washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The resulting crude crystals were recrystallized from diisopropyl ether, to give 3.37 g of the title compound as white needles.

Workup

  1. temperatureUnder ice-cooling
  2. temperaturecooled
  3. customaluminium hydroxide was precipitated
  4. customthe organic layer was decanted
  5. additionTo the residue was added 20 ml of tetrahydrofuran
  6. stirringstirred
  7. customthe organic layer was re-decanted twice
  8. customThe solvent was evaporated from the collected organic layers
  9. dissolutionThe residue was dissolved in 80 ml of ethyl acetate
  10. washthe mixture was sequentially washed with water and brine
  11. dry with materialdried over anhydrous magnesium sulfate
  12. customthe solvent was evaporated
  13. customThe resulting crude crystals were recrystallized from diisopropyl ether

Sources & evidence

ORD record
ord-6657fcd43bb4411dafeaa73f025393d0
Source dataset
uspto-grants-2009_06
Patent number
US07541376B2

Reaction notes

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