Ethyl Acetate → HCID 135869969, compound

HRID 1873969Notes

Reaction equation

HRID 1873969 reaction equation
[Si]([O:18][C:19]1[CH:27]=[C:26]2[C:22]([C:23]([Cl:35])=[N:24][N:25]2[C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])=[CH:21][CH:20]=1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-].C1COCC1.C(OCC)(=O)C>C1COCC1>[Cl:35][C:23]1[C:22]2[C:26](=[CH:27][C:19]([OH:18])=[CH:20][CH:21]=2)[N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[N:24]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11078149TBAF tetrahydrofuranHCID 45280190HCID 45280190, compound

Product 1

HCID 135869969HCID 135869969, compoundYield 69.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Tert-butyl 6-(tert-butyldiphenylsilyloxy)-3-chloroindazole-1-carboxylate (17.415 g) which can be prepared according to the method described in Reference example 38, etc. was dissolved in dehydrated THF (150 mL), added with 1 mol/L-TBAF-THF solution (42 mL; manufactured by Tokyo Chemical Industry, Co., Ltd.), and stirred overnight at room temperature. The reaction solution was added with ethyl acetate and the organic layer was washed once with brine, once with water, and once with brine and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, the resulting residue was added with n-hexane (150 mL) and the suspension was subjected to ultrasonication treatment. The precipitate was filtered to obtain the title compound (6.3815 g).

Workup

  1. washthe organic layer was washed once with brine, once with water
  2. dry with materialonce with brine and dried over anhydrous sodium sulfate
  3. customAfter the solvent was evaporated under reduced pressure
  4. additionthe resulting residue was added with n-hexane (150 mL)
  5. customthe suspension was subjected to ultrasonication treatment
  6. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-da755b0d679a4486ae9754e192b72531
Source dataset
uspto-grants-2012_11
Patent number
US08304443B2

Reaction notes

Loading…