Triacetoxyperiodinane → (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone

HRID 563367Notes

Reaction equation

HRID 563367 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]([CH:17]([C:19]4[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=4)[OH:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:4][CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[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]([C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=4)=[O:18])=[CH:14][CH:15]=3)[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 59251034(1-(4-Fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol

Product 1

HCID 67005723(1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanoneYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanol (1.2 g, 3.77 mmol) from experimental (1f) in 200 mL of CH2Cl2 was added Dess-Martin Periodinane (2.0 g, 4.71 mmol) portionwise. After 12 h, the reaction was quenched with 1M NaOH and extracted with 3×CH2Cl2. The CH2Cl2 extracts were dried over MgSO4, filtered, and concentrated by rotary evaporator to give (1-(4-fluorophenyl)-1H-indazol-5-yl)(phenyl)methanone in 100% yield. MS found: (M+H)+=317.

Workup

  1. customthe reaction was quenched with 1M NaOH
  2. extractionextracted with 3×CH2Cl2
  3. dry with materialThe CH2Cl2 extracts were dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporator

Sources & evidence

ORD record
ord-aaf1fe9a78fa4497854a76b3fa8416de
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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