Ammonium Chloride → 3-iodo-1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-amine

HRID 706741Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 706741
[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-])=O)[N:4]([CH2:14][C:15]2[S:19][C:18]([CH3:20])=[N:17][CH:16]=2)[N:3]=1.[Cl-].[NH4+]>CCO.O.[Fe]>[I:1][C:2]1[C:10]2[C:9]([NH2:11])=[CH:8][CH:7]=[CH:6][C:5]=2[N:4]([CH2:14][C:15]2[S:19][C:18]([CH3:20])=[N:17][CH:16]=2)[N:3]=1

Komponenten

5

Edukt 2

HCID 25517Ammonium ChlorideHCID 679761065-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-2-methylthiazole

Produkt 1

HCID 672609553-iodo-1-((2-methylthiazol-5-yl)methyl)-1H-indazol-4-amineAusbeute 99,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
85 °C

Versuchsvorschrift

To a solution of 5-((3-iodo-4-nitro-1H-indazol-1-yl)methyl)-2-methylthiazole (332 mg, 0.830 mmol) in EtOH/water (4:1, 10 mL) was added iron powder (463 mg, 8.30 mmol) and ammonium chloride (44.4 mg, 0.83 mmol). The resulting mixture was heated at 85° C. with vigorous magnetic stirring for three hours. The mixture was cooled to ambient temperature, concentrated, and EtOAc (40 mL) and triethylamine (10 mL) were added. The resulting mixture was heated at 85° C. for 20 minutes, then cooled to 45° C., filtered through a Celite plug, and the plug was rinsed with MeOH (30 mL). The combined organic filtrates were concentrated, the residue was extracted with DCM (3×30 mL), the combined organic extracts dried over sodium sulfate, filtered and concentrated to afford the desired product (307 mg).

Aufarbeitung

  1. temperatureThe mixture was cooled to ambient temperature
  2. concentrationconcentrated
  3. additionEtOAc (40 mL) and triethylamine (10 mL) were added
  4. temperatureThe resulting mixture was heated at 85° C. for 20 minutes
  5. temperaturecooled to 45° C.
  6. filtrationfiltered through a Celite plug
  7. washthe plug was rinsed with MeOH (30 mL)
  8. concentrationThe combined organic filtrates were concentrated
  9. extractionthe residue was extracted with DCM (3×30 mL)
  10. dry with materialthe combined organic extracts dried over sodium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-c64442782f0648b3a4230b0363e5599c
Quelldatensatz
uspto-grants-2015_11
Patentnummer
US09174981B2

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