Water → HCID 135869959, compound

HRID 1873949Notes

Reaction equation

HRID 1873949 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([O:17][Si](C(C)(C)C)(C3C=CC=CC=3)C3C=CC=CC=3)[CH:15]=2)[C:10]([CH:35]2[CH2:38][CH2:37][CH2:36]2)=[N:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.O>C1COCC1.[Cl-].[Na+].O>[C:1]([O:5][C:6]([N:8]1[C:16]2[C:11](=[CH:12][CH:13]=[C:14]([OH:17])[CH:15]=2)[C:10]([CH:35]2[CH2:36][CH2:37][CH2:38]2)=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 45280131HCID 45280131, compound

Product 1

HCID 135869959HCID 135869959, compoundYield 96%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Tert-butyl6-(tert-butyldiphenylsilyloxy)-3-cyclobutylindazole-1-carboxylate (12.26 g) which can be prepared according to the method described in Reference example 13, etc. was dissolved in THF (83 mL; manufactured by Kanto Chemical Co., Inc.). Then, 1 mol/L-TBAF-THF solution (46 mL) was added and the mixture was stirred for 1 hour at room temperature. To the reaction solution, water and brine were added and extraction was carried out three times with ethyl acetate. The organic layer was washed with water and brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=95:5→74:26) to obtain the title compound (6.4457 g).

Workup

  1. extractionextraction
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customAfter the solvent was evaporated under reduced pressure
  5. customthe residue was purified by column chromatography (“COLUMN-B”; n-hexane:ethyl acetate=95:5→74:26)

Sources & evidence

ORD record
ord-a199b34ca49644e48a044785ee7d7016
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

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