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

HRID 1477856Notes

Reaction equation

HRID 1477856 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([N:35]2[C:43]3[C:38](=[C:39]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH:40]=[CH:41][CH:42]=3)[CH:37]=[N:36]2)([CH2:33][CH3:34])[CH2:31][OH:32])=[CH:26][CH:25]=1>C(Cl)Cl>[Cl:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]([N:35]2[C:43]3[C:38](=[C:39]([NH:44][C:45](=[O:51])[O:46][C:47]([CH3:50])([CH3:49])[CH3:48])[CH:40]=[CH:41][CH:42]=3)[CH:37]=[N:36]2)([CH2:33][CH3:34])[CH:31]=[O:32])=[CH:26][CH:25]=1

Participants

4

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 70560487tert-butyl 1-(2-(4-chlorophenyl)-1-hydroxybutan-2-yl)-1H-indazol-4-ylcarbamate

Product 1

HCID 86705040tert-butyl 1-[2-(4-chlorophenyl)-1-oxobutan-2-yl]-1H-indazol-4-ylcarbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of Dess-Martin periodinane (8.12 g, 19.15 mmol) in DCM (90 mL) at 0° C. was added a solution of tert-butyl 1-[2-(4-chlorophenyl)-1-hydroxybutan-2-yl]-1H-indazol-4-ylcarbamate (3.18 g, 7.67 mmol) in DCM (20 mL). The mixture was allowed to stir at rt for 2 hours. Then it was filtered and the filtrate was concentrated in vacuo to afford the crude product. The product was purified via column chromatography (0-10% EtOAc/hexanes) to provide the desired product.

Workup

  1. filtrationThen it was filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customto afford the crude product
  4. customThe product was purified via column chromatography (0-10% EtOAc/hexanes)

Sources & evidence

ORD record
ord-8c56e16632744f40a30ba7dbea43e773
Source dataset
uspto-grants-2016_08
Patent number
US09403807B2

Reaction notes

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