3-Chloro-N-methoxy-N-methylpyrazine-2-carboxamide → [4-(Benzyloxy)phenyl](3-chloropyrazin-2-yl)methanone

HRID 573311Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573311
[Cl:1][C:2]1[C:3]([C:8](N(OC)C)=[O:9])=[N:4][CH:5]=[CH:6][N:7]=1.[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([Mg]Br)=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>C1COCC1>[CH2:14]([O:21][C:22]1[CH:27]=[CH:26][C:25]([C:8]([C:3]2[C:2]([Cl:1])=[N:7][CH:6]=[CH:5][N:4]=2)=[O:9])=[CH:24][CH:23]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Komponenten

4

Edukt 2

HCID 534175293-Chloro-N-methoxy-N-methylpyrazine-2-carboxamideHCID 178419638HCID 178419638, Verbindung

Produkt 1

HCID 86688975[4-(Benzyloxy)phenyl](3-chloropyrazin-2-yl)methanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-chloro-N-methoxy-N-methylpyrazine-2-carboxamide (2.05 g) in THF (50 mL) was added dropwise [4-(benzyloxy)phenyl]magnesium bromide in THF (12 mL) at 0° C. After stirring at 0° C. for 2 h, the mixture was quenched with water and extracted with AcOEt. The organic layer was washed with brine, dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (AcOEt/hexane) to give the title compound (2.47 g).

Aufarbeitung

  1. customthe mixture was quenched with water
  2. extractionextracted with AcOEt
  3. washThe organic layer was washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (AcOEt/hexane)

Quellen und Nachweise

ORD-Eintrag
ord-c8087302b1f44c80af4ed5eeb2214e86
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029536B2

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