Sodium periodate → 1-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methanesulfinyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

HRID 1515725Notes

Reaction equation

HRID 1515725 reaction equation
I([O-])(=O)(=O)=[O:2].[Na+].[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]2[CH:19]=[C:18]([C:20]([C:27]3[CH:28]=[N:29][C:30]([S:33][CH3:34])=[CH:31][CH:32]=3)=[CH:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[N:17]([S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)(=[O:37])=[O:36])[C:14]2=[N:15][CH:16]=1)=[O:10]>O.CO>[CH3:7][O:8][C:9]([C:11]1[CH:12]=[C:13]2[CH:19]=[C:18]([C:20]([C:27]3[CH:28]=[N:29][C:30]([S:33]([CH3:34])=[O:2])=[CH:31][CH:32]=3)=[CH:21][CH:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[N:17]([S:35]([C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)(=[O:37])=[O:36])[C:14]2=[N:15][CH:16]=1)=[O:10]

Participants

5

Reactant 2

HCID 23667635Sodium periodateHCID 672292131-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methylsulfanyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester

Product 1

HCID 672279081-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methanesulfinyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl esterYield 97.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of sodium metaperiodate (360 mg, 1.69 mmol) in water (10 ml) was added a solution of 1-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methylsulfanyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (300 mg, 0.56 mmol) in methanol (40 ml). The reaction mixture was stirred at 25° C. for 60 h. The suspension was filtered. The filtrate was concentrated and extracted with ethyl acetate (2×30 mL). The combined organic extracts were washed with water (2×20 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 1-benzenesulfonyl-2-[2-cyclopentyl-1-(6-methanesulfinyl-pyridin-3-yl)-vinyl]-1H-pyrrolo[2,3-b]pyridin-5-carboxylic acid methyl ester (301 mg, 97%) as a solid which was used in the next step without further purification: LC/MS m/e calcd for C28H27N3O5S2 [M+H]+ 550.67, observed 549.9.

Workup

  1. filtrationThe suspension was filtered
  2. concentrationThe filtrate was concentrated
  3. extractionextracted with ethyl acetate (2×30 mL)
  4. washThe combined organic extracts were washed with water (2×20 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-92b04b56a1c74e818c3ebb6c7cdb1f43
Source dataset
uspto-grants-2012_07
Patent number
US08222416B2

Reaction notes

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