Water → 1-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

HRID 69247

Reaktionsgleichung

Reaktionsgleichung von HRID 69247
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH:10]=[O:11])=[CH:2]1.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[OH-].[Na+].O>C(Cl)Cl.S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18]([N:1]2[C:5]3=[N:6][CH:7]=[CH:8][CH:9]=[C:4]3[C:3]([CH:10]=[O:11])=[CH:2]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 7369Benzenesulfonyl chlorideHCID 14798Sodium HydroxideHCID 53728121H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde

Produkt 1

HCID 103566461-(Phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

1H-Pyrrolo[2,3-b]pyridine-3-carbaldehyde (200 mg, 1.368 mmol) was dissolved in DCM (8 mL). Then tetra-n-butylammonium hydrogen sulfate (48.4 mg, 0.137 mmol), benzensulfonyl chloride (0.176 mL, 1.37 mmol) and NaOH 50% (0.263 mL, 3.3 mmol) were added. The RM was stirred at rt for 1 h. Water was added and it was extracted with DCM twice. The combined organic layers was washed with brine and dried over Na2SO4, filtered and evaporated to afford the title compound as a light yellow solid (tR 2.0 min (conditions 1), MH+=287).

Aufarbeitung

  1. extractionit was extracted with DCM twice
  2. washThe combined organic layers was washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-920a061c2d4f423bb73537e9753053e2
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08822468B2

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