Ammonium Chloride → 1-(2-(6-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one

HRID 1400908Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1400908
[F:1][C:2]1[CH:31]=[C:30]([N+:32]([O-])=O)[CH:29]=[CH:28][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]4[CH2:26][CH2:25][CH2:24][C:23]4=[O:27])=[CH:16][CH:15]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CCO.[Zn].[Fe]>[NH2:32][C:30]1[CH:29]=[CH:28][C:3]([O:4][C:5]2[CH:10]=[CH:9][N:8]=[C:7]3[CH:11]=[C:12]([C:14]4[N:19]=[CH:18][C:17]([CH2:20][CH2:21][N:22]5[CH2:26][CH2:25][CH2:24][C:23]5=[O:27])=[CH:16][CH:15]=4)[S:13][C:6]=23)=[C:2]([F:1])[CH:31]=1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 584745171-(2-(6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-one

Produkt 1

HCID 584747051-(2-(6-(7-(4-Amino-2-fluorophenoxy)thieno[3,2-b]pyridin-2-yl)pyridin-3-yl)ethyl)pyrrolidin-2-oneAusbeute 46 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 23994ZincKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

To impure 293 (0.76 g, 1.6 mmol) in EtOH (75 mL) was added zinc dust (1.04 g, 15.9 mmol), iron filings (0.89 g, 16 mmol) and saturated aqueous ammonium chloride solution (2 mL). The resultant mixture was heated to reflux for 18 h, then cooled, filtered through celite, concentrated and re-dissolved in dichloromethane. The solution was washed with water, 1 M NaOH, and brine, dried (anhydrous MgSO4), filtered, concentrated and the residue was purified by silica gel chromatography (15% MeOH/chloroform) to afford title compound 294 (0.33 g, 46% yield). MS (M+H): 449.2

Aufarbeitung

  1. temperatureto reflux for 18 h
  2. temperaturecooled
  3. filtrationfiltered through celite,
  4. concentrationconcentrated
  5. dissolutionre-dissolved in dichloromethane
  6. washThe solution was washed with water, 1 M NaOH, and brine
  7. dry with materialdried (anhydrous MgSO4)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customthe residue was purified by silica gel chromatography (15% MeOH/chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-d6481775f9194642b5f4ce310f0cdc52
Quelldatensatz
uspto-grants-2014_12
Patentnummer
US08906852B2

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