Trifluoroacetic acid → 4-propoxy-1H-indazol-5-ol

HRID 1269934Notes

Reaction equation

HRID 1269934 reaction equation
FC(F)(F)C(O)=O.[CH2:8]([O:11][C:12]1[C:20]([O:21]C2CCCCO2)=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[N:15][N:16]2C1CCCCO1)[CH2:9][CH3:10].[OH-].[Na+]>ClCCl>[CH2:8]([O:11][C:12]1[C:20]([OH:21])=[CH:19][CH:18]=[C:17]2[C:13]=1[CH:14]=[N:15][NH:16]2)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 694345664-propoxy-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole

Product 1

HCID 229337144-propoxy-1H-indazol-5-olYield 74,384.797%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Under a nitrogen atmosphere, trifluoroacetic acid (5.5 ml) was added to a solution of 4-propoxy-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (852.6 mg) in dichloromethane (16.5 ml) at room temperature. After 2.5 hours, the reaction solution was poured onto ice, adjusted to pH 7 with an aqueous sodium hydroxide solution, and then extracted with ethyl acetate. The extract solution was concentrated under reduced pressure and the resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate). The residue purified was concentrated under reduced pressure and the resulting residue was washed with diethyl ether/hexane by repulping to obtain 4-propoxy-1H-indazol-5-ol (338.2 g, 80%, two steps).

Workup

  1. additionthe reaction solution was poured onto ice
  2. extractionextracted with ethyl acetate
  3. concentrationThe extract solution was concentrated under reduced pressure
  4. customthe resulting residue was purified by a silica gel column chromatography (eluent: hexane/ethyl acetate)
  5. customThe residue purified
  6. concentrationwas concentrated under reduced pressure
  7. washthe resulting residue was washed with diethyl ether/hexane

Sources & evidence

ORD record
ord-bc89269cc3b3465ea29b2845a3e92621
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

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