N-bromobutanimide → 3-bromo-1H-indole-5-sulfonamide

HRID 528844Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528844
[NH:1]1[C:9]2[C:4](=[CH:5][C:6]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:7][CH:8]=2)[CH:3]=[CH:2]1.[Br:14]N1C(=O)CCC1=O>CN(C=O)C.OS([O-])=O.[Na+].CCOC(C)=O>[Br:14][C:3]1[C:4]2[C:9](=[CH:8][CH:7]=[C:6]([S:10]([NH2:13])(=[O:11])=[O:12])[CH:5]=2)[NH:1][CH:2]=1

Komponenten

6

Edukt 2

HCID 67184N-bromobutanimideHCID 216831001H-Indole-5-sulfonamide2×

Produkt 1

HCID 710624653-bromo-1H-indole-5-sulfonamideAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 23665763Sodium BisulfiteLösungsmittel

Versuchsvorschrift

To a solution of 1H-indole-5-sulfonamide (Intermediate 54, 100 mg, 0.51 mmol) in DMF (2.0 mL) was added N-bromosuccinimide (91 mg, 0.51 mmol) at 0° C. The resulting reaction mixture was stirred at room temperature for 30 min and then diluted with sat. aq. NaHSO3 solution and EtOAc. The organic layer was washed with sat. aq. NaCl solution, dried over MgSO4, filtered and concentrated in vacuo. The residue was purified using preparative HPLC to give the title compound (90 mg, 61%) as a white solid after lyophilization. 1H NMR (DMSO-d6) δ 11.88 (br s, 1H), 7.94 (d, J=8.1 Hz, 1H), 7.75 (d, J=2.6 Hz, 1H), 7.65-7.63 (m, 1H), 7.59-7.57 (m, 1H), 7.21 (s, 2H); MS (ESI+) m/z 277.1 (M+H)+.

Aufarbeitung

  1. customThe resulting reaction mixture
  2. washThe organic layer was washed with sat. aq. NaCl solution
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified

Quellen und Nachweise

ORD-Eintrag
ord-4efca17a3b5547229b59fd1a626a7eeb
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346795B2

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