Sodium periodate → HCID 59437310, compound

HRID 244432Notes

Reaction equation

HRID 244432 reaction equation
[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]3[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=3)[N:26]=[CH:25]4)([OH:21])[C:17]([F:20])([F:19])[F:18])=[CH:7][N:8]2[CH2:11][CH:12]([OH:15])CO)=[CH:4][CH:3]=1.I([O-])(=O)(=O)=O.[Na+]>CC(C)=O.O>[Br:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:16]([C:22]3[CH:23]=[C:24]4[C:28](=[CH:29][CH:30]=3)[N:27]([C:31]3[CH:32]=[CH:33][C:34]([F:37])=[CH:35][CH:36]=3)[N:26]=[CH:25]4)([OH:21])[C:17]([F:18])([F:19])[F:20])=[CH:7][N:8]2[CH2:11][CH:12]=[O:15])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 24957618HCID 24957618, compound

Product 1

HCID 59437310HCID 59437310, compoundYield 84.5%

Reagents, catalysts & solvents 1

HCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

To a room temperature solution of 75 mg (0.13 mmol) of 3-(6-bromo-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)propane-1,2-diol in acetone-H2O (3:1) was added 34.2 mg (0.16 mmol) of sodium periodate. After 2 hours, the mixture was concentrated in vacuo. The residue was basified and extracted with ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to afford 60 mg (71%) of (6-bromo-3-{2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]-1-hydroxyethyl}indol-1-yl)acetaldehyde. MS m/z 547.31 (MH+).

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-79d5edcaf12d47feb09ce5cd170f371a
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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