3,4-dihydro-2H-pyran → 4-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

HRID 475161Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475161
[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][NH:6]2.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1>C1COCC1>[Br:1][C:2]1[CH:10]=[C:9]([O:11][CH3:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[N:5][N:6]2[CH:14]1[CH2:15][CH2:16][CH2:17][CH2:18][O:13]1

Komponenten

4

Edukt 2

HCID 80803,4-dihydro-2H-pyranHCID 247283154-Bromo-6-methoxy-1H-indazole

Produkt 1

HCID 712726524-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazoleAusbeute 111,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A round-bottom flask was charged with 4-bromo-6-methoxy-1H-indazole (1.00 g, 4.40 mmol), TsOH monohydrate (39 mg, 0.22 mmol), 3,4-dihydro-2H-pyran (1.48 g, 17.6 mmol), and THF (40 mL). The reaction mixture was degassed with nitrogen and refluxed for 18 h, and the solvent was then removed in vacuo. The residue was purified by SiO2 chromatography to afford 4-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.53 g, quantitative) as a yellow solid. MS (ESI) m/z: 311.2 [M+1]+.

Aufarbeitung

  1. customThe reaction mixture was degassed with nitrogen
  2. temperaturerefluxed for 18 h
  3. customthe solvent was then removed in vacuo
  4. customThe residue was purified by SiO2 chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7cd624c9808944f895df6a8821c90150
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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