Tetrabutylammonium Fluoride → tert-Butyl 5-hydroxy-3-iodo-1H-indazole-1-carboxylate

HRID 246719

Reaction equation

HRID 246719 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])[N:13]=[C:12]2[I:25])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([C:18]([O:20][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:19])[N:13]=[C:12]2[I:25]

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 71279782HCID 71279782, compound

Product 1

HCID 71280823tert-Butyl 5-hydroxy-3-iodo-1H-indazole-1-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred solution of tert-butyl 5-(tert-butyldimethylsilyloxy)-3-iodo-1H-indazole-1-carboxylate (1 g, 2.11 mmol) in THF (10 mL), was added TBAF (5.6 g, 21.1 mmol) in THF (5 mL). The mixture was stirred at room temperature for 0.5 hour. The solvent was removed under reduced pressure. The residue was diluted with water and extracted with EtOAc (3×10 mL). The combined organic layers were washed with brine and dried over Na2SO4. After filtration and concentration, the crude product was used in the next step without purification. LCMS: 361 [M+H]+.

Workup

  1. customThe solvent was removed under reduced pressure
  2. additionThe residue was diluted with water
  3. extractionextracted with EtOAc (3×10 mL)
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationAfter filtration and concentration
  7. customthe crude product was used in the next step without purification

Sources & evidence

ORD record
ord-8d543d0f60504360a6a41e959910119b
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Linked notes

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