Potassium Carbonate → tert-Butyl 4-(6-nitro-1H-indazol-1-yl)piperidine-1-carboxylate

HRID 515377

Reaktionsgleichung

Reaktionsgleichung von HRID 515377
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][NH:10]2)=[CH:6][CH:5]=1)([O-:3])=[O:2].CS(O[CH:18]1[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]1)(=O)=O.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH:8]=[N:9][N:10]2[CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:25])[CH2:20][CH2:19]2)=[CH:6][CH:5]=1)([O-:3])=[O:2]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 242396-NitroindazoleHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidine

Produkt 1

HCID 68609514tert-Butyl 4-(6-nitro-1H-indazol-1-yl)piperidine-1-carboxylateAusbeute 24,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

6-Nitro-1H-indazole (12.26 mmol, 2 g), tert-butyl 4-(methylsulfonyloxy)piperidine-1-carboxylate (12.26 mmol, 3.42 g) and potassium carbonate (24.52 mmol, 3.39 g) were combined and heated to 100° C. in N,N-dimethylformamide (40 mL) for 4 hours. The reaction mixture was diluted with ethyl acetate and washed with water. The organic phase was dried over sodium sulfate and concentrated at reduced pressure. The resulting residue was purified by silica chromatography (eluting with a solvent gradient from 20% ethyl acetate/heptane to 60% ethyl acetate/heptane) to afford the title compound (1.045 g). MS (ESI) m/z 347.2 [M+H]+

Aufarbeitung

  1. washwashed with water
  2. dry with materialThe organic phase was dried over sodium sulfate
  3. concentrationconcentrated at reduced pressure
  4. customThe resulting residue was purified by silica chromatography (
  5. washeluting with a solvent gradient from 20% ethyl acetate/heptane to 60% ethyl acetate/heptane)

Quellen und Nachweise

ORD-Eintrag
ord-fca53bf4e3b2464b842024cedb7bc183
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09108939B2

Verknüpfte Notizen

Wird geladen…