Ammonium Chloride → 4-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroaniline

HRID 347516Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 347516
[F:1][C:2]1[CH:17]=[C:16]([N+:18]([O-])=O)[CH:15]=[CH:14][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[NH:11][CH:12]=[CH:13][C:6]=12.[Cl-].[NH4+]>O1CCCC1.CO.[Zn]>[NH:11]1[C:7]2=[N:8][CH:9]=[CH:10][C:5]([O:4][C:3]3[CH:14]=[CH:15][C:16]([NH2:18])=[CH:17][C:2]=3[F:1])=[C:6]2[CH:13]=[CH:12]1

Komponenten

6

Edukt 2

HCID 25517Ammonium ChlorideHCID 210816364-(2-Fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-B]pyridine

Produkt 1

HCID 160379654-((1H-Pyrrolo[2,3-B]pyridin-4-YL)oxy)-3-fluoroanilineAusbeute 77 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23994ZincKatalysatorHCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a suspension of 4-(2-fluoro-4-nitrophenoxy)-1H-pyrrolo[2,3-b]pyridine (300 mg, 1.1 mmol) in tetrahydrofuran (5 mL) and methanol (10 mL), were added zinc powder (350 mg, 5.5 mmol) and ammonium chloride (294 mg, 5.5 mmol). The mixture was stirred at rt overnight. The mixture was filtered through a pad of Celite®, rinsed with methanol. The filtrate was concentrated. The product was purified by flash column chromatography (silica gel, 1–5% MeOH in CH2Cl2) to afford the desired product (205 mg, 77%) as an off-white solid. MS(ESI+) m/z 244 (M+H)+.

Aufarbeitung

  1. filtrationThe mixture was filtered through a pad of Celite®
  2. washrinsed with methanol
  3. concentrationThe filtrate was concentrated
  4. customThe product was purified by flash column chromatography (silica gel, 1–5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-457e7633c2c34709a97827f9aa4a2157
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07173031B2

Notizen zur Reaktion

Wird geladen…