Triacetoxyperiodinane → tert-butyl 1-(2-(4-chlorophenyl)-4,4,4-trifluoro-1-oxobutan-2-yl)-1H-indazol-4-ylcarbamate

HRID 1477904Notes

Reaction equation

HRID 1477904 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH2:11][C:12]([F:15])([F:14])[F:13])[CH2:9][OH:10])=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl.O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([N:16]2[C:24]3[C:19](=[C:20]([NH:25][C:26](=[O:32])[O:27][C:28]([CH3:30])([CH3:29])[CH3:31])[CH:21]=[CH:22][CH:23]=3)[CH:18]=[N:17]2)([CH2:11][C:12]([F:14])([F:15])[F:13])[CH:9]=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 70561960tert-butyl 1-(2-(4-chlorophenyl)-4,4,4-trifluoro-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

Product 1

HCID 86705054tert-butyl 1-(2-(4-chlorophenyl)-4,4,4-trifluoro-1-oxobutan-2-yl)-1H-indazol-4-ylcarbamate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the product of Step B (200 mg, 0.42 mmol) in DCM (5 mL) was added Dess-Martin periodinane (350 mg, 0.84 mmol) in portion at room temperature. The mixture was stirred at for 0.5 h, and then diluted with water (5 mL), extracted with ethyl acetate. The organic layers were washed with brine (5 mL), dried over sodium sulfate, filtered and evaporated. The residue was purified by silica gel chromatography (EA/PE=1:8) to afford the title compound. LC/MS m/z=468.2[M+H]+.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layers were washed with brine (5 mL)
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by silica gel chromatography (EA/PE=1:8)

Sources & evidence

ORD record
ord-8b45fcb611984ccc9c76cd5d08af63c0
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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