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Potassium Carbonate → N-[2,4-Difluoro-3-[[5-(3-pyridinyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl]phenyl]-2-propanesulfonamide

HRID 249814
Notes
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Reaction equation

HRID 249814 reaction equation
[F:1][C:2]1[C:7]([CH:8]([OH:24])[C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[NH:11][CH:10]=2)=[C:6]([F:25])[CH:5]=[CH:4][C:3]=1[NH:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28].CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C1=CC=CC=2)=O.S([O-])([O-])(=O)=S.[Na+].[Na+].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[F:1][C:2]1[C:7]([C:8]([C:9]2[C:17]3[C:12](=[N:13][CH:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[NH:11][CH:10]=2)=[O:24])=[C:6]([F:25])[CH:5]=[CH:4][C:3]=1[NH:26][S:27]([CH:30]([CH3:32])[CH3:31])(=[O:29])=[O:28]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 58086871HCID 58086871, compound

Product 1

HCID 53438230N-[2,4-Difluoro-3-[[5-(3-pyridinyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]carbonyl]phenyl]-2-propanesulfonamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To propane-2-sulfonic acid {2,4-difluoro-3-[hydroxy-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridin-3-yl)-methyl]-phenyl}-amide (50, 40.0 mg, 0.087 mmol) in tetrahydrofuran (10 mL) was added Dess-Martin periodane (48.0 mg, 0.11 mmol). The reaction was stirred at room temperature for 5 minutes. The reaction was poured into sodium thiosulfate and potassium carbonate solution and extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and filtrated. The filtrate was concentrated and purified by silica gel column chromatography eluting with 5% methanol in methylene chloride to give the compound (51, 13.4 mg, 33.5%). MS (ESI) [M+H+]+=458.1.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated
  6. custompurified by silica gel column chromatography
  7. washeluting with 5% methanol in methylene chloride
  8. customto give the compound (51, 13.4 mg, 33.5%)

Sources & evidence

ORD record
ord-ec1fe3b3c0984e128a2cbc2e328132df
Source dataset
uspto-grants-2011_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07863289B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes