Water → 2-{[3-(Azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile

HRID 1874920Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1874920
Br[CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[C:13]([Cl:19])[N:12]=2)[C:6]([Cl:9])=[CH:7][CH:8]=1.[N-:21]=[N+:22]=[N-:23].[Na+].O.C([O-])(O)=O.[Na+]>CS(C)=O>[N:21]([CH2:2][C:3]1[C:4]([F:20])=[C:5]([O:10][C:11]2[CH:16]=[C:15]([C:17]#[N:18])[CH:14]=[C:13]([Cl:19])[N:12]=2)[C:6]([Cl:9])=[CH:7][CH:8]=1)=[N+:22]=[N-:23]

Komponenten

6

Edukt 4

HCID 962WaterHCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 86644895HCID 86644895, Verbindung

Produkt 1

HCID 866448962-{[3-(Azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrileAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

2-{[3-(bromomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (2.00 g, 5.32 mmol) and sodium azide (0.346 g, 5.32 mmol) were combined in DMSO (10 mL) and stirred 16 h at 25° C. at which time TLC indicated complete conversion (10% Et2O/hexanes). Water (150 mL) and saturated aqueous NaHCO3 (30 mL) were added and the mixture stirred vigorously for 30 min. The resultant precipitate was filtered off, washed with water, and air dried to give 2-{[3-(azidomethyl)-6-chloro-2-fluorophenyl]oxy}-6-chloro-4-pyridinecarbonitrile (1.76 g, 5.21 mmol, 98% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.01 (d, J=0.73 Hz, 1H), 7.96 (d, J=0.73 Hz, 1H), 7.48-7.60 (m, 2H), 4.60 (s, 2H).

Aufarbeitung

  1. stirringthe mixture stirred vigorously for 30 min
  2. filtrationThe resultant precipitate was filtered off
  3. washwashed with water, and air
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-20e0dab825194fd2a9fa74c82d6ee2c2
Quelldatensatz
uspto-grants-2012_11
Patentnummer
US08304419B2

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