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Sodium Iodide → 4-(4-oxo-1-(tetrahydrofuran-3-yl)-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)benzenesulfonamide

HRID 2206010
Notes
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Reaction equation

HRID 2206010 reaction equation
C[O:2][C:3]1[C:8]2[C:9]([C:17]3[CH:22]=[CH:21][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:19][CH:18]=3)=[CH:10][N:11]([CH:12]3[CH2:16][CH2:15][O:14][CH2:13]3)[C:7]=2[CH:6]=[CH:5][N:4]=1.[I-].[Na+].Cl[Si](C)(C)C.C(=O)([O-])O.[Na+]>C(#N)C>[O:2]=[C:3]1[C:8]2[C:9]([C:17]3[CH:18]=[CH:19][C:20]([S:23]([NH2:26])(=[O:25])=[O:24])=[CH:21][CH:22]=3)=[CH:10][N:11]([CH:12]3[CH2:16][CH2:15][O:14][CH2:13]3)[C:7]=2[CH:6]=[CH:5][NH:4]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 6397ChlorotrimethylsilaneHCID 516892Sodium BicarbonateHCID 1179880584-(4-methoxy-1-(tetrahydrofuran-3-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl)benzenesulfonamide

Product 1

HCID 1179877644-(4-oxo-1-(tetrahydrofuran-3-yl)-4,5-dihydro-1H-pyrrolo[3,2-c]pyridin-3-yl)benzenesulfonamideYield 67.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-(4-methoxy-1-(tetrahydrofuran-3-yl)-1H-pyrrolo[3,2-c]pyridin-3-yl)benzenesulfonamide (17.1 mg) in acetonitrile (2 mL) were added sodium iodide (17.1 mg) and chloro(trimethyl)silane (0.058 mL), and the mixture was stirred overnight at 50° C. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol) to give the title compound (11.1 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate to ethyl acetate/methanol)

Sources & evidence

ORD record
ord-83560102fe094fc39881b03d007a5bbd
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09371320B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes