Tetrahydrofuran → 2-(benzyloxy)-4-(3,4-difluoro-1H-pyrrol-1-yl)aniline

HRID 1528057Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1528057
C1COCC1.[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([N:23]2[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24]2)[CH:17]=[CH:18][C:19]=1[N+:20]([O-])=O)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>[Zn].C(O)(=O)C>[CH2:6]([O:13][C:14]1[CH:15]=[C:16]([N:23]2[CH:27]=[C:26]([F:28])[C:25]([F:29])=[CH:24]2)[CH:17]=[CH:18][C:19]=1[NH2:20])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Komponenten

5

Edukt 2

HCID 8028Tetrahydrofuran2×HCID 712722201-[3-(benzyloxy)-4-nitrophenyl]-3,4-difluoro-1H-pyrrole

Produkt 1

HCID 866865492-(benzyloxy)-4-(3,4-difluoro-1H-pyrrol-1-yl)anilineAusbeute 97,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 176Acetic AcidLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of zinc (33.7 g), THF (40 mL) and acetic acid (80 mL) was added dropwise a mixture of 1-[3-(benzyloxy)-4-nitrophenyl]-3,4-difluoro-1H-pyrrole (8.52 g), THF (80 mL) and acetic acid (40 mL) at 0° C., and the mixture was stirred at 0° C. for 15 min. The reaction mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized from hexane/ethyl acetate to give the title compound (7.53 g).

Aufarbeitung

  1. additionwas added dropwise
  2. filtrationThe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  5. customrecrystallized from hexane/ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-fd6d4008a0b54f8199876b4b1ae94bc0
Quelldatensatz
uspto-grants-2015_07
Patentnummer
US09090586B2

Notizen zur Reaktion

Wird geladen…