Benzenesulfonyl chloride → HCID 49758931, Verbindung

HRID 1020906Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1020906
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][N:9]=[C:8]2[C:4]=1[CH:5]=[CH:6][NH:7]2.[C:12]1([S:18](Cl)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>ClCCl.[OH-].[Na+].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[C:12]1([S:18]([N:7]2[C:8]3[C:4](=[C:3]([O:2][CH3:1])[CH:11]=[CH:10][N:9]=3)[CH:5]=[CH:6]2)(=[O:20])=[O:19])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Komponenten

6

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 112405674-Methoxy-1H-pyrrolo[2,3-b]pyridine

Produkt 1

HCID 49758931HCID 49758931, VerbindungAusbeute 73,9 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 74236Tetrabutylammonium BromideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

To a mixture of 4-methoxy-7-azaindole (6.4 g, 43.2 mmol) in dichloromethane (200 mL) and 50% aqueous sodium hydroxide (200 mL) was added benzenesulfonyl chloride (6.1 mL, 47.5 mmol) and tetrabutylammonium bromide (1.4 g, 4.3 mmol). The mixture was stirred vigorously at room temperature for 18 hours. The organic phase was washed with water and brine, dried (MgSO4), filtered and concentrated. The crude product was recrystallized from ethyl acetate and hexanes to give 9.2 g of 1-benzenesulfonyl-4-methoxy-7-azaindole as a yellow solid. 1H NMR (DMSO-d6) δ 8.30 (d, J=5 Hz, 1H), 8.18 (d, 1 Hz, 1H), 7.58 (m, 2H), 7.47 (m, 2H), 6.67 (d, 4 Hz, 1H), 6.61 (d, 4 Hz, 1H), 3.94 (s, 3H). MS (m/z) 289 (M+H).

Aufarbeitung

  1. washThe organic phase was washed with water and brine
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was recrystallized from ethyl acetate and hexanes

Quellen und Nachweise

ORD-Eintrag
ord-5038c587efa045b88c5723d41efc326f
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08716493B2

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