3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal → 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanoic acid

HRID 563399Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:22])([CH3:21])[CH2:18][CH:19]=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC(C)=[O:25].OS(O)(=O)=O.O=[Cr](=O)=O>CC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[C:16]3[C:11](=[CH:12][C:13]([C:17]([CH3:22])([CH3:21])[CH2:18][C:19]([OH:25])=[O:20])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of the above 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanal in acetone (3 mL) was added Jones' reagent (1 mL) dropwise at 0° C. The reaction mixture was stirred at 0° C. for 30 min before being concentrated under reduced pressure. The residue was neutralized with saturated aqueous sodium bicarbonate solution and 10% aqueous citric acid solution, and then extracted with ethyl acetate (3×10 mL). The combined ethyl acetate extracts were dried (Na2SO4), concentrated and purified by reverse phase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA) to give 3-(1-(4-fluorophenyl)-1H-indazol-5-yl)-3-methylbutanoic acid (100 mg, 0.32 mmol, 43% yield for 2 steps) as a yellow oil.

Workup

concentrationbefore being concentrated under reduced pressure
extractionextracted with ethyl acetate (3×10 mL)
dry with materialThe combined ethyl acetate extracts were dried (Na2SO4)
concentrationconcentrated
custompurified by reverse phase HPLC (YMC S5 20×100 mm, 10 min. run, solvent A: 10% MeOH: 90% H2O: 0.1% TFA, solvent B: 90% MeOH, 10% H2O, 0.1% TFA)

Sources & evidence

ORD record: ord-2198d1dcaccc4dff9e28923e055703ce
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08067447B2

Reaction notes

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