N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxvmethyl-3-trifluoromethyl-benzenesulfonamide → 4-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-Pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide

HRID 1898121Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1898121
Br[C:2]1[C:7]([N:8]([CH2:23][O:24][CH3:25])[S:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[C:14]([C:19]([F:22])([F:21])[F:20])[CH:13]=2)(=[O:11])=[O:10])=[CH:6][C:5]([Cl:26])=[CH:4][N:3]=1.C([Mg]Cl)(C)C.CON(C)[C:35](=[O:47])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=1[C:42]1[O:43][CH:44]=[CH:45][N:46]=1>C1COCC1>[Cl:18][C:15]1[CH:16]=[CH:17][C:12]([S:9]([N:8]([C:7]2[C:2]([C:35](=[O:47])[C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][C:37]=3[C:42]3[O:43][CH:44]=[CH:45][N:46]=3)=[N:3][CH:4]=[C:5]([Cl:26])[CH:6]=2)[CH2:23][O:24][CH3:25])(=[O:11])=[O:10])=[CH:13][C:14]=1[C:19]([F:22])([F:21])[F:20]

Komponenten

5

Edukt 3

HCID 57942086N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxvmethyl-3-trifluoromethyl-benzenesulfonamideHCID 57942199N-Methoxy-N-methyl-2-oxazol-2-yl-benzamideHCID 178418918HCID 178418918, Verbindung

Produkt 1

HCID 579423584-Chloro-N-[5-chloro-2-(2-oxazol-2-yl-benzoyl)-Pyridin-3-yl]-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamideAusbeute 20,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of N-(2-Bromo-5-chloro-pyridin-3-yl)-4-chloro-N-methoxymethyl-3-trifluoromethyl-benzenesulfonamide (125 mg, 0.25 mmol) in 2.0 mL of THF under nitrogen atmosphere at 0° C. was added drop-wise 0.3 ml (0.6 mmol) of isopropylmagnesium chloride. The mixture was then stirred for 20 min at 0° C. followed by addition of N-Methoxy-N-methyl-2-oxazol-2-yl-benzamide (100 mg, 0.43 mmol). The mixture was stirred at room temperature overnight, quenched with saturated ammonium chloride and extracted with ethyl acetate. After concentration the residue was purified by flash chromatograph (30% ethyl acetate in hexane) to afford 30 mg of title compound as an off white solid. MS: (M+H)/z=586.1.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature overnight
  2. customquenched with saturated ammonium chloride
  3. extractionextracted with ethyl acetate
  4. concentrationAfter concentration the residue
  5. customwas purified by flash chromatograph (30% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-fc7251f665c3443c85419436d99892d1
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08519135B2

Notizen zur Reaktion

Wird geladen…