o-Toluenesulfonyl chloride → HCID 49758932, Verbindung

HRID 1409108Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1409108
[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[NH:9][CH:10]=[CH:11][C:3]=12.[H-].[Na+].[C:14]1(C)[C:15]([S:20](Cl)(=[O:22])=[O:21])=[CH:16][CH:17]=[CH:18][CH:19]=1.[CH3:25]COC(C)=O>CN(C=O)C>[Br:1][C:2]1[C:7]([Cl:8])=[CH:6][N:5]=[C:4]2[N:9]([S:20]([C:15]3[CH:14]=[CH:19][C:18]([CH3:25])=[CH:17][CH:16]=3)(=[O:21])=[O:22])[CH:10]=[CH:11][C:3]=12

Komponenten

6

Edukt 4

HCID 8623o-Toluenesulfonyl chlorideHCID 8857Ethyl AcetateHCID 24758Sodium hydride2×HCID 468355224-Bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 49758932HCID 49758932, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 4-bromo-5-chloro-1H-pyrrolo[2,3-b]pyridine (D) (1.89 g, 8.16 mmol) in DMF (15 mL) at 0° C. was added NaH (60% in oil, 328 mg) followed by toluenesulfonylchloride (1.72 g, 8.98 mmol). The reaction mixture was warmed to RT and additional NaH (60% in oil, 2×200 mg) was added at 1 h intervals. After a further 1 h, EtOAc was added and the reaction was quenched with sat'd NaHCO3. The aqueous layer was extracted with EtOAc and the combined organic layer was washed with water, brine, dried over Na2SO4, filtered and concentrated. Flash chromatography (SiO2, 7% EtOAc in hexanes) provided 4-bromo-5-chloro-1-tosyl-1H-pyrrolo[2,3-b]pyridine (E) (1.81 g, 58%) as an off white solid. LC/MS Tret=4.8 min, (M+H+) 386.6.

Aufarbeitung

  1. customthe reaction was quenched with sat'd NaHCO3
  2. extractionThe aqueous layer was extracted with EtOAc
  3. washthe combined organic layer was washed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-efdc30931e6f4d3bb80dbc35aa63f81c
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921376B2

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