Water → 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

HRID 475121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 475121
[I:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[NH:4][N:3]=1.[O:13]1[CH:18]=[CH:17][CH2:16][CH2:15][CH2:14]1.CC1C=CC(S(O)(=O)=O)=CC=1.O>C1COCC1>[I:1][C:2]1[C:10]2[C:9]([C:11]#[N:12])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH:14]2[CH2:15][CH2:16][CH2:17][CH2:18][O:13]2)[N:3]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 80803,4-dihydro-2H-pyranHCID 1785096383-Iodo-1H-indazole-4-carbonitrile

Produkt 1

HCID 712725503-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrileAusbeute 84,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

A mixture of 3-iodo-1H-indazole-4-carbonitrile (3.0 g, 11.1 mmol), dihydropyran (1.84 g, 22.2 mmol), and TsOH (212 mg, 1.1 mmol) under nitrogen in THF (40 mL) was heated at 85° C. overnight. Water (40 mL) was added and the mixture was extracted with EtOAc (50 mL×3). The combined extracts were washed with brine, dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (5:1) to afford 3-iodo-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as white solid (3.31 g, 84.0%). MS (ESI): m/z=354 [M+1]+.

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc (50 mL×3)
  2. washThe combined extracts were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by SiO2 chromatography
  7. washeluting with petroleum ether/EtOAc (5:1)

Quellen und Nachweise

ORD-Eintrag
ord-3ca3fa32512e4f80bcbf3ea31b984ebb
Quelldatensatz
uspto-grants-2014_01
Patentnummer
US08637537B2

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