Ammonium Chloride → 2-Fluoro-N1-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamine

HRID 1711105Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1711105
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=3)[S:20][C:13]=12.[NH4+].[Cl-]>CO.O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=3)[S:20][C:13]=12

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 59457676N-(2-Fluoro-4-nitrophenyl)-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-amine

Produkt 1

HCID 594577422-Fluoro-N1-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamineAusbeute 136,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

To a stirred suspension of nitro compound 417 (370 mg, 1.00 mmol) in a mixture of MeOH (20 mL) and water (10 mL) were added iron powder (280 mg, 5.01 mmol) and NH4Cl (107 mg, 2.00 mmol). The reaction mixture was heated to reflux for 2 hrs, cooled to room temperature and filtered through celite. The filtrate was concentrated, diluted with minimal amount of methanol and treated with AcOEt/hexanes, to afford title compound 418 (463 mg, quantitative yield, ammonium salt) as a yellow solid. LCMS: 340.0 (M+H)+.

Aufarbeitung

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hrs
  3. filtrationfiltered through celite
  4. concentrationThe filtrate was concentrated
  5. additiondiluted with minimal amount of methanol
  6. additiontreated with AcOEt/hexanes

Quellen und Nachweise

ORD-Eintrag
ord-cd749d74a89e44f49c76f6b91194a9ee
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07790729B2

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