Triphenylphosphine → 6-(3,5-difluorophenyl)-2-[3-(5-methylpyridin-2-yl)benzyl]-2H-pyridazin-3-one

HRID 1408389

Reaktionsgleichung

Reaktionsgleichung von HRID 1408389
N(C(OC(C)C)=O)=NC(OC(C)C)=O.[CH3:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]2[CH:23]=[C:24]([CH2:28]O)[CH:25]=[CH:26][CH:27]=2)=[N:20][CH:21]=1.[F:30][C:31]1[CH:32]=[C:33]([C:38]2[CH:39]=[CH:40][C:41](=[O:44])[NH:42][N:43]=2)[CH:34]=[C:35]([F:37])[CH:36]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>C1COCC1>[F:30][C:31]1[CH:32]=[C:33]([C:38]2[CH:39]=[CH:40][C:41](=[O:44])[N:42]([CH2:28][C:24]3[CH:25]=[CH:26][CH:27]=[C:22]([C:19]4[CH:18]=[CH:17][C:16]([CH3:15])=[CH:21][N:20]=4)[CH:23]=3)[N:43]=2)[CH:34]=[C:35]([F:37])[CH:36]=1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 25241749HCID 25241749, VerbindungHCID 56604357(3-(5-Methylpyridin-2-yl)phenyl)methanol

Produkt 1

HCID 594848946-(3,5-difluorophenyl)-2-[3-(5-methylpyridin-2-yl)benzyl]-2H-pyridazin-3-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

4.2 134 mg (0.66 mmol) of diisopropyl azodicarboxylate are added to a solution of 88 mg (0.44 mmol) of [3-(5-methylpyridin-2-yl)phenyl]methanol, 138 mg (0.66 mmol) of 6-(3,5-difluorophenyl)-2H-pyridazin-3-one and 174 mg (0.66 mmol) of triphenylphosphine in 3.5 ml of THF. The reaction mixture is stirred at room temperature for 18 hours. The mixture is evaporated, and the residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent: 6-(3,5-difluorophenyl)-2-[3-(5-methylpyridin-2-yl)benzyl]-2H-pyridazin-3-one (“A9”) as colourless crystals; ESI 390.

Aufarbeitung

  1. customThe mixture is evaporated
  2. customthe residue is chromatographed on a silica gel column with dichloromethane/methanol as eluent

Quellen und Nachweise

ORD-Eintrag
ord-d9f3a906aada457db5444dbcb73fdcff
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08921357B2

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