Trifluoroacetic acid → HCID 22933604, compound

HRID 1269969Notes

Reaction equation

HRID 1269969 reaction equation
[CH:1]([C:4]1[C:12]([O:13]C2CCCCO2)=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][N:8]2C1CCCCO1)([CH3:3])[CH3:2].C(C1C(O)=CC=C2C=1C=NN2C1CCCCO1)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])O.[Na+]>ClCCl.C(OCC)(=O)C>[CH:1]([C:4]1[C:12]([OH:13])=[CH:11][CH:10]=[C:9]2[C:5]=1[CH:6]=[N:7][NH:8]2)([CH3:3])[CH3:2]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 69430803HCID 69430803, compoundHCID 69434565HCID 69434565, compound

Product 1

HCID 22933604HCID 22933604, compoundYield 280.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 4-isopropyl-1-tetrahydro-2H-pyran-2-yl-5-(tetrahydro-2H-pyran-2-yloxy)-1H-indazole (301 mg, 0.871 mmol) and 4-isopropyl-1-tetrahydro-2H-pyran-2-yl-1H-indazol-5-ol (586 mg, 2.25 mmol) was made into a solution of the mixture in dichloromethane (26 ml), followed by adding thereto trifluoroacetic acid (6.5 ml), and the resulting mixture was stirred for 4 hours while being maintained at room temperature. The reaction solution was diluted with ethyl acetate, neutralized with a saturated aqueous sodium hydrogencarbonate solution and extracted with ethyl acetate, and the extract solution was dried over anhydrous magnesium sulfate and filtered. The filtrate was concentrated under reduced pressure to obtain a crude product. The crude product was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate) to obtain 4-isopropyl-1H-indazol-5-ol (430 mg, 78%).

Workup

  1. additionby adding
  2. extractionextracted with ethyl acetate
  3. dry with materialthe extract solution was dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customto obtain a crude product
  7. customThe crude product was purified by a silica gel column chromatography (eluent: chloroform/ethyl acetate)

Sources & evidence

ORD record
ord-59ddc9401e264665877768fa05df2bc3
Source dataset
uspto-grants-2007_04
Patent number
US07199147B2

Reaction notes

Loading…