Sodium periodate → HCID 86654499, compound

HRID 1515612Notes

Reaction equation

HRID 1515612 reaction equation
[CH:1]1([CH2:6][CH:7]([C:18]2[NH:30][C:21]3=[N:22][CH:23]=[C:24]([CH:26]([OH:29])CO)[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.I([O-])(=O)(=O)=O.[Na+]>O1CCCC1>[CH:1]1([CH2:6][CH:7]([C:18]2[NH:30][C:21]3=[N:22][CH:23]=[C:24]([CH:26]=[O:29])[CH:25]=[C:20]3[CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH3:17])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 23667635Sodium periodateHCID 532502881-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethane-1,2-diol

Product 1

HCID 86654499HCID 86654499, compoundYield 99.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of a diastereomeric mixture of 1-{2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-yl}-ethane-1,2-diol (366 mg, 0.86 mmol) in 50% aqueous tetrahydrofuran (10 mL) was added sodium metaperiodate (366 mg, 1.71 mmol) at 0° C. The resulting mixture was stirred at room temperature for 2 h and extracted with ethyl acetate and washed with brine, dried over anhydrous sodium sulfate. The solvent was evaporated in vacuo to give 2-[2-cyclopentyl-1-(4-methanesulfonyl-phenyl)-ethyl]-1H-pyrrolo[2,3-b]pyridin-5-carbaldehyde (340 mg, quant.) as a light yellow solid: LC/MS m/e calcd for C22H24N2OS [M+H]+ 397.51, observed 397.0.

Workup

  1. extractionextracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-e5c2849627b14a97a6a45e015cfcf322
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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