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Dimethylformamide → 6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile

HRID 475162
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 475162
Br[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:13]1[CH2:18][CH2:17][CH2:16][CH2:15][O:14]1.[CH3:19][N:20](C=O)C>[C-]#N.[C-]#N.[Zn+2].C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:12][O:11][C:9]1[CH:10]=[C:2]([C:19]#[N:20])[C:3]2[CH:4]=[N:5][N:6]([CH:13]3[CH2:18][CH2:17][CH2:16][CH2:15][O:14]3)[C:7]=2[CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 6228DimethylformamideHCID 712726524-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole

Produkt 1

HCID 866947116-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrileAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 11186Zinc cyanide (Zn(CN)2)Katalysator
HCID 178418397
HCID 178418397, Verbindung
Katalysator

Reaktionsbedingungen

Temperatur
145 °C

Versuchsvorschrift

A sealed microwave vial was charged with 4-bromo-6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole (1.50 g, 4.82 mmol), Zn(CN)2 (0.62 g, 5.30 mmol), Pd(PPh3)4 (0.22 g, 0.19 mmol), and DMF (13 mL). The mixture was degassed for 5 min under nitrogen and then heated in a microwave reactor at 145° C. for 25 min. The mixture was diluted with EtOAc and filtered. The filtrate was partitioned between water and EtOAc, and the layers were separated. The organic layer was washed with water (3×), dried (Na2SO4), filtered, and concentrated in vacuo. The crude mixture was purified by SiO2 chromatography to afford 6-methoxy-1-(tetrahydro-2H-pyran-2-yl)-1H-indazole-4-carbonitrile as a solid (1.06 g, 86%). MS (ESI) m/z: 258.2 [M+1]+.

Aufarbeitung

  1. customThe mixture was degassed for 5 min under nitrogen
  2. additionThe mixture was diluted with EtOAc
  3. filtrationfiltered
  4. customThe filtrate was partitioned between water and EtOAc
  5. customthe layers were separated
  6. washThe organic layer was washed with water (3×)
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude mixture was purified by SiO2 chromatography

Quellen und Nachweise

ORD-Eintrag
ord-21c7529ae68c47449bb2c436c7520d4b
Quelldatensatz
uspto-grants-2014_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08637537B2

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