Triacetoxyperiodinane → HCID 86710007, compound

HRID 508206Notes

Reaction equation

HRID 508206 reaction equation
[Cl:1][C:2]1[CH:36]=[CH:35][CH:34]=[C:33]([C:37]([F:40])([F:39])[F:38])[C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:30]=[CH:29][C:18]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:17]([CH2:31][OH:32])[CH:16]=2)=[N:7]1)=[O:5].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:36]=[CH:35][CH:34]=[C:33]([C:37]([F:39])([F:38])[F:40])[C:3]=1[C:4]([N:6]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][CH:13]=2)[C:8]([C:15]2[CH:30]=[CH:29][C:18]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[C:17]([CH:31]=[O:32])[CH:16]=2)=[N:7]1)=[O:5]

Participants

5

Reactant 2

HCID 159087TriacetoxyperiodinaneHCID 68279036HCID 68279036, compound

Product 1

HCID 86710007HCID 86710007, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of benzyl 4-(1-(2-chloro-6-(trifluoromethyl)benzoyl)-1H-indazol-3-yl)-2-(hydroxymethyl)benzoate (G-3) (0.4 g, 0.71 mmol) in DCM (10 mL) was added Dess-Martin periodinane (0.45 g, 1.07 mmol), and the mixture was stirred at rt for 24 h. The mixture was diluted with H2O and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resulting crude oil was used in the next step without further purification. LCMS (ESI)′ calc'd for C30H19ClF3N2O4 [M+H]+: 563. found: 563.

Workup

  1. extractionextracted with DCM
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated
  5. customThe resulting crude oil was used in the next step without further purification

Sources & evidence

ORD record
ord-d632bfd73feb4e52b46375d4c90a0c8a
Source dataset
uspto-grants-2015_08
Patent number
US09095583B2

Reaction notes

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