Water → HCID 135869950, compound

HRID 1873945Notes

Reaction equation

HRID 1873945 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[CH2:37][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]2)=[N:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 962WaterHCID 11078149TBAF tetrahydrofuranHCID 45280078HCID 45280078, compound

Product 1

HCID 135869950HCID 135869950, compoundYield 93.5%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Tert-butyl6-(tert-butyldiphenylsilyloxy)-3-cyclopropylindazole-1-carboxylate (5.08 g) which can be prepared according to the method described in Reference example 6, etc. was dissolved in THF (53 mL; manufactured by Kanto Chemical Co., Inc.), and added with 1 mol/L-TBAF-THF solution (19.82 mL), followed by stirring at room temperature for 0.5 hours. To the reaction solution, water and brine were added and extraction was carried out three times with ethyl acetate. The organic layer was washed 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 (2.54 g).

Workup

  1. extractionextraction
  2. washThe organic layer was washed 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-3488b7c2376044279d4ab229ac156a5c
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

Loading…