Pyridine → 5-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzene

HRID 1167489

Reaktionsgleichung

Reaktionsgleichung von HRID 1167489
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]2)=[C:6]([F:8])[CH:7]=1.N1C=CC=CC=1.Cl[C:22]([O:24][CH2:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:23].C(=O)(O)[O-].[Na+]>ClCCl>[CH2:25]([O:24][C:22]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([N:9]2[CH:13]=[C:12]([CH3:14])[N:11]=[CH:10]2)=[C:6]([F:8])[CH:7]=1)=[O:23])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10387Benzyl chloroformateHCID 516892Sodium BicarbonateHCID 218766383-Fluoro-4-(4-methyl-1H-imidazol-1-yl)aniline

Produkt 1

HCID 218766725-Benzyloxycarbonylamino-2-(4-methylimidazol-1-yl)fluorobenzeneAusbeute 92,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

5-Amino-2-(4-methyl-imidazol-1-yl)fluorobenzene (50.6 g, 0.265 M) was dissolved in dry dichloromethane (800 ml) under nitrogen, and cooled to −5°. Pyridine (26.1 g, 0.33 M) was added, followed by benzyl chloroformate (49.9 g, 0.292 M) over 30 minutes. The mixture was stirred and the temperature allowed to rise to ambient over 16 hours. Aqueous sodium bicarbonate (5%, 350 ml) was added, the organic layer separated, and the aqueous layer re-extracted with dichloromethane (2×200 ml), and combined organics dried (magnesium sulfate). After filtration and evaporation, the residue was recrystallised from toluene (300 ml) to give title product (80 g).

Aufarbeitung

  1. temperaturecooled to −5°
  2. customthe organic layer separated
  3. extractionthe aqueous layer re-extracted with dichloromethane (2×200 ml)
  4. dry with materialcombined organics dried (magnesium sulfate)
  5. filtrationAfter filtration and evaporation
  6. customthe residue was recrystallised from toluene (300 ml)

Quellen und Nachweise

ORD-Eintrag
ord-bbba7690b4b444d3ba23a5bb0ae30385
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06617339B1

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