1-Methylimidazole → 3-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamide

HRID 573618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 573618
Br[C:2]1[S:22][C:5]2=[N:6][C:7]([CH3:21])=[CH:8][C:9]([NH:10][S:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([Cl:20])[CH:15]=3)(=[O:13])=[O:12])=[C:4]2[C:3]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=1.[CH3:31][N:32]1C=CN=C1>[Fe-4](C#N)(C#N)(C#N)(C#N)(C#N)C#N.[K+].[K+].[K+].[K+].[Cu]I>[Cl:20][C:16]1[CH:15]=[C:14]([S:11]([NH:10][C:9]2[CH:8]=[C:7]([CH3:21])[N:6]=[C:5]3[S:22][C:2]([C:31]#[N:32])=[C:3]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([O:29][CH3:30])[CH:24]=4)[C:4]=23)(=[O:13])=[O:12])[CH:19]=[CH:18][CH:17]=1

Komponenten

5

Edukt 2

HCID 13901-MethylimidazoleHCID 53250396N-{2-Bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide

Produkt 1

HCID 683240723-Chloro-N-{2-cyano-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-benzenesulfonamideAusbeute 74,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 178511492HCID 178511492, VerbindungKatalysator2×

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

Alternatively, a mixture of N-{2-bromo-6-methyl-3-[3-(methyloxy)phenyl]thieno[2,3-b]pyridin-4-yl}-3-chlorobenzenesulfonamide (310 mg, 0.592 mmol) (Example 33), potassium ferrocyanide (50.0 mg, 0.118 mmol), copper(I) iodide (11.27 mg, 0.059 mmol) in 1-methylimidazole (3 mL, 37.6 mmol) was heated at 160° C. for 2 h. Extra potassium ferrocyanide (100 mg, 0.118 mmol) was added and heating continued at 160° C. for 21 h. The mixture was then cooled to RT. Purification by chromatography on silica gel, eluting with a gradient of 0-60% ethyl acetate in cyclohexane, afforded the title compound (208 mg).

Aufarbeitung

  1. temperatureheating
  2. temperatureThe mixture was then cooled to RT
  3. customPurification by chromatography on silica gel
  4. washeluting with a gradient of 0-60% ethyl acetate in cyclohexane

Quellen und Nachweise

ORD-Eintrag
ord-0a7df37e293941fda35c29fefd006ced
Quelldatensatz
uspto-grants-2015_05
Patentnummer
US09029545B2

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