Water → 3-Iodo-1-methyl-1H-indazol-5-ol

HRID 246615Notes

Reaction equation

HRID 246615 reaction equation
[Si]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][CH:17]=1)[N:14]([CH3:18])[N:13]=[C:12]2[I:19])(C(C)(C)C)(C)C.CCCC[N+](CCCC)(CCCC)CCCC.[F-].O>C1COCC1>[I:19][C:12]1[C:11]2[C:15](=[CH:16][CH:17]=[C:9]([OH:8])[CH:10]=2)[N:14]([CH3:18])[N:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 712798665-((tert-Butyldimethylsilyl)oxy)-3-iodo-1-methyl-1H-indazole

Product 1

HCID 712797213-Iodo-1-methyl-1H-indazol-5-olYield 120.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(tert-butyldimethylsilyloxy)-3-iodo-1-methyl-1H-indazole (1 g, 2.57 mmol) in THF (5 mL) was added TBAF (6.42 mL, 12.85 mmol) at 0° C., after the addition, the reaction mixture was warmed to room temperature and stirred for 0.5 hour, then H2O (25 mL) was added to the mixture and product extracted with EtOAc (100 mL). The organic layer was washed with H2O (100 mL), brine (100 mL), dried over Na2SO4 and concentrated under reduced pressure, the residue was triturated with petroleum ether (5 mL), filtered and dried to give 3-iodo-1-methyl-1H-indazol-5-ol (0.85 g, 93.3%) as a white solid. Crude material used into the next step without further purification. LCMS: (M+H)+=275.

Workup

  1. additionafter the addition
  2. extractionextracted with EtOAc (100 mL)
  3. washThe organic layer was washed with H2O (100 mL), brine (100 mL)
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customthe residue was triturated with petroleum ether (5 mL)
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-20005cc252234a39a4d30a9279a8817d
Source dataset
uspto-grants-2014_02
Patent number
US08658646B2

Reaction notes

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