Ammonium Chloride → 1-[8-Amino-2-(4-fluorophenyl)imidazo[1,2-a)pyridin-3-yl]ethanone

HRID 456685Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 456685
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]3[C:15]([N+:16]([O-])=O)=[CH:14][CH:13]=[CH:12][N:11]3[C:19]=2[C:20](=[O:22])[CH3:21])=[CH:4][CH:3]=1.[Cl-].[NH4+]>CO.[Fe]>[NH2:16][C:15]1[C:10]2[N:11]([C:19]([C:20](=[O:22])[CH3:21])=[C:8]([C:5]3[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=3)[N:9]=2)[CH:12]=[CH:13][CH:14]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 695493021-[2-(4-Fluorophenyl)-8-nitroimidazo[1,2-a]pyridin-3-yl]ethanone

Produkt 1

HCID 695497661-[8-Amino-2-(4-fluorophenyl)imidazo[1,2-a)pyridin-3-yl]ethanoneAusbeute 70,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 887MethanolLösungsmittel2×

Versuchsvorschrift

A solution of 1-[2-(4-fluorophenyl)-8-nitroimidazo[1,2-α]pyridin-3-yl]ethanone (100 mg, 0.33 mmol) in methanol (3 mL) was added to a suspension of iron (93 mg, 1.7 mmol) and ammonium chloride (149 mg, 2.8 mmol) in aqueous methanol. This reaction mixture was heated to reflux for 10 hours. The reaction mixture was filtered and the filtrate concentrated under reduced pressure to a solid. This solid was purified by silica gel chromatography (5% methanol in dichloromethane) to give 63 mg (70%) of 1-[8-amino-2-(4-fluorophenyl)imidazo[1,2-α]pyridin-3-yl]ethanone as a foam. 1H NMR (CDCl3): δ 9.21 (d, 1H), 7.61 (m, 2H), 7.25 (m, 2H), 6.94 (t, 1H) 6.72 (d, 1H), 4.63 (broad s, 2H), 2.19 (s, 3H); MS m/z 270 (M+1).

Aufarbeitung

  1. temperatureThis reaction mixture was heated
  2. temperatureto reflux for 10 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate concentrated under reduced pressure to a solid
  5. customThis solid was purified by silica gel chromatography (5% methanol in dichloromethane)

Quellen und Nachweise

ORD-Eintrag
ord-ae9679ebf79f4ee5b567661d24151925
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07186714B2

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