N-bromobutanimide → 3-Bromo-5-cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazole

HRID 63533Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 63533
[CH:1]1([C:4]2[C:12]([N+:13]([O-:15])=[O:14])=[CH:11][C:10]3[C:6](=[CH:7][N:8]([C:16]4[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=4)[N:9]=3)[CH:5]=2)[CH2:3][CH2:2]1.[Br:23]N1C(=O)CCC1=O>CN(C=O)C>[Br:23][C:7]1[N:8]([C:16]2[CH:21]=[CH:20][C:19]([CH3:22])=[CH:18][N:17]=2)[N:9]=[C:10]2[C:6]=1[CH:5]=[C:4]([CH:1]1[CH2:3][CH2:2]1)[C:12]([N+:13]([O-:15])=[O:14])=[CH:11]2

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 866989485-Cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazole

Produkt 1

HCID 866989493-Bromo-5-cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazoleAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a solution of (ii) (1.08 g, 3.67 mmol) in DMF (15 mL) was added N-bromosuccinimide (780 mg, 4.40 mmol) and the resulting mixture stirred at 80° C. for 1.5 h. The reaction mixture was then cooled to RT and the solvent was removed under reduced pressure. The residue was dissolved in EtOAc (100 mL) and washed with aq. saturated sodium bicarbonate (20 mL) and brine (20 mL). The organic phase was dried (MgSO4) and the volatiles removed in vacuo to give (iii) (1.37 g, >99%). ESI-MS: calculated [M+H]+ 373.01375.0. observed [M+H]+ 373.1/375.1.

Aufarbeitung

  1. temperatureThe reaction mixture was then cooled to RT
  2. customthe solvent was removed under reduced pressure
  3. dissolutionThe residue was dissolved in EtOAc (100 mL)
  4. washwashed with aq. saturated sodium bicarbonate (20 mL) and brine (20 mL)
  5. dry with materialThe organic phase was dried (MgSO4)
  6. customthe volatiles removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e65bb998b6db4aa2915061dc575f6af6
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09447080B2

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