Methanol → N-[(2-Chloropyridin-4-yl)(2-cyano-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamide

HRID 1662216Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1662216
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=O)[CH:5]=[CH:4][N:3]=1.[CH3:19][C:20]([S:23]([NH2:25])=[O:24])([CH3:22])[CH3:21].CO.C(=O)(O)[O-].[Na+]>C1COCC1>[Cl:1][C:2]1[CH:7]=[C:6]([C:8]([C:10]2[CH:17]=[CH:16][CH:15]=[C:14]([F:18])[C:11]=2[C:12]#[N:13])=[N:25][S:23]([C:20]([CH3:22])([CH3:21])[CH3:19])=[O:24])[CH:5]=[CH:4][N:3]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 3382465Tert-ButanesulfinamideHCID 585795302-(2-Chloro-pyridine-4-carbonyl)-6-fluorobenzonitrile

Produkt 1

HCID 76821601N-[(2-Chloropyridin-4-yl)(2-cyano-3-fluorophenyl)methylidene]-2-methylpropane-2-sulfinamideAusbeute 48 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Ti(OEt)4 (15 mL) was added to a solution of 2-(2-chloro-pyridine-4-carbonyl)-6-fluoro-benzonitrile (3.6 g, 13.81 mmol) and 2-methyl-propane-2-sulfinic acid amide (2.5 g, 20.72 mmol) in dry THF (100 mL) at room temperature. The resulting mixture was stirred to reflux for 40 hours and then treated with CH3OH (50 mL) and saturated sodium bicarbonate solution (10 mL). The resulting suspension was filtered through a pad of Celite® and the solids were washed with THF (50 mL) and CH3OH (20 mL). The filtrate was concentrated under reduced pressure and the residue was purified by flash column chromatography using a gradient of 25-50% EtOAc in hexane to afford the title compound (2.4 g, 48%).

Aufarbeitung

  1. temperatureto reflux for 40 hours
  2. filtrationThe resulting suspension was filtered through a pad of Celite®
  3. washthe solids were washed with THF (50 mL) and CH3OH (20 mL)
  4. concentrationThe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-541ade82e0ef4ed28067e695e121ca90
Quelldatensatz
uspto-grants-2011_10
Patentnummer
US08030500B2

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