Water → 5-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridine

HRID 269489Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 269489
[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][NH:8][C:5]2=[N:6][CH:7]=1.[H-].[Na+].[CH3:13][S:14](Cl)(=[O:16])=[O:15].O>C1COCC1>[Br:1][C:2]1[CH:3]=[C:4]2[CH:10]=[CH:9][N:8]([S:14]([CH3:13])(=[O:16])=[O:15])[C:5]2=[N:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 31297Methanesulfonyl chlorideHCID 103079325-bromo-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 497588975-Bromo-1-(methanesulfonyl)-1H-pyrrolo[2,3-b]pyridineAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 5-bromo-1H-pyrrolo[2,3-b]pyridine (600 mg, 3.06 mmol) in dry THF (30 mL) was added NaH (246 mg, 6.12 mmol) at room temperature. The suspension was stirred for 30 min before addition of methanesulfonyl chloride (540 mg, 4.80 mmol). The solution was stirred at room temperature for another 30 min and poured into water (50 mL). The aqueous solution was extracted with ethyl acetate (2×30 mL), the combined organic layers were dried over MgSO4 and filtered, the filtrate was evaporated under vacuum to afford white solid (780 mg, 93%). The crude product was used directly for the next reaction. LC/MS: Rt 3.26 mis.; (m/e=275.0, 276.9 (M+H, M+2+H).

Aufarbeitung

  1. extractionThe aqueous solution was extracted with ethyl acetate (2×30 mL)
  2. dry with materialthe combined organic layers were dried over MgSO4
  3. filtrationfiltered
  4. customthe filtrate was evaporated under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-b52bd419eb1f4f729888f8c98810de78
Quelldatensatz
uspto-grants-2008_11
Patentnummer
US07446199B2

Notizen zur Reaktion

Wird geladen…