Bromine → HCID 178477911, Verbindung

HRID 879415Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 879415
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[NH:7][N:6]=[CH:5]2.[Br:11]Br.[O-]S([O-])(=S)=O.[Na+].[Na+]>CN(C=O)C>[Br:11][C:5]1[C:4]2[C:8](=[CH:9][CH:10]=[C:2]([Cl:1])[CH:3]=2)[NH:7][N:6]=1

Komponenten

5

Edukt 3

HCID 24408Bromine2×HCID 24477Sodium ThiosulfateHCID 696811H-Indazole, 5-chloro-

Produkt 1

HCID 178477911HCID 178477911, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

A flask was charged with 5-chloro-1H-indazole (4.9 g, 32.11 mmol) and DMF (30 mL). It was then cooled to 0° C., and a solution of bromine (2.4 mL, 46.86 mmol) in DMF (30 mL) was added over several minutes. After addition was complete, the flask was warmed to rt and stirred for 4 hours. Additional bromine (0.89 mL, 16 mmol) was added, and the reaction stirred at room temperature for 20 minutes. The reaction was poured into 600 mL of ice-cold 1% (w/v) Na2S2O3 solution, and the precipitated product was filtered off. The product was redissolved in EtOAc (500 mL), washed with saturated aqueous NaHCO3 then brine, dried over Na2SO4, and concentrated to afford the product. 1H NMR (400 MHz, DMSO-d6) δ 13.60 (br s, 1H), 7.68-7.54 (m, 2H), 7.44 (dd, J=9.0, 1.8 Hz, 1H).

Aufarbeitung

  1. additionAfter addition
  2. temperaturethe flask was warmed to rt
  3. stirringthe reaction stirred at room temperature for 20 minutes
  4. filtrationthe precipitated product was filtered off
  5. dissolutionThe product was redissolved in EtOAc (500 mL)
  6. washwashed with saturated aqueous NaHCO3
  7. dry with materialbrine, dried over Na2SO4
  8. concentrationconcentrated
  9. customto afford the product

Quellen und Nachweise

ORD-Eintrag
ord-01db81e944454514bfb81c27d945d406
Quelldatensatz
uspto-grants-2015_03
Patentnummer
US08987250B2

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