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Imidazole → Ethyl6-tert-butyldiphenylsilyloxyindazole-3-carboxylate

HRID 1873952
Notes
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Reaction equation

HRID 1873952 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([OH:15])=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:5])[CH3:2].N1C=CN=C1.[CH3:21][C:22]([Si:25](Cl)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([CH3:24])[CH3:23].C(=O)([O-])O.[Na+]>CN(C=O)C>[CH2:1]([O:3][C:4]([C:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][Si:25]([C:22]([CH3:24])([CH3:23])[CH3:21])([C:32]3[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=3)[C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:12][CH:13]=2)[NH:8][N:7]=1)=[O:5])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 795ImidazoleHCID 94078tert-ButyldiphenylchlorosilaneHCID 516892Sodium BicarbonateHCID 136205193Ethyl6-hydroxyindazole-3-carboxylate

Product 1

HCID 59370747Ethyl6-tert-butyldiphenylsilyloxyindazole-3-carboxylate

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

Ethyl6-hydroxyindazole-3-carboxylate (1.457 g) which can be prepared according to the method described in Reference example 17, etc. was dissolved in dehydrated DMF (15.6 mL; manufactured by Kanto Chemical Co., Inc.), added with imidazole (1.425 g; manufactured by Tokyo Chemical Industry, Co., Ltd.) and TBDPSCl (4.06 mL), followed by stirring overnight at room temperature. The reaction solution was poured to a saturated aqueous solution of sodium hydrogen carbonate and extracted twice with ethyl acetate. The organic layer was washed with brine and insoluble matters were filtered using Celite. The organic layer was washed twice with water and dried over anhydrous magnesium sulfate. After the solvent was evaporated under reduced pressure, the residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=81:19→60:40) to obtain the title compound (1.467 g).

Workup

  1. extractionextracted twice with ethyl acetate
  2. washThe organic layer was washed with brine and insoluble matters
  3. filtrationwere filtered
  4. washThe organic layer was washed twice with water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customAfter the solvent was evaporated under reduced pressure
  7. customthe residue was purified by column chromatography (“COLUMN-A”; n-hexane:ethyl acetate=81:19→60:40)

Sources & evidence

ORD record
ord-38cad0cf7fa947208ec6c5f596b575e3
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08304443B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes