(4-Methoxyphenyl)boronic acid → 5-(4-Methoxyphenyl)pyridin-2(1H)-one

HRID 1948198

Reaktionsgleichung

Reaktionsgleichung von HRID 1948198
Br[C:2]1[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=1.[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1>C1CCCCC1.CCOC(C)=O>[CH3:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([C:2]2[CH:3]=[CH:4][C:5](=[O:8])[NH:6][CH:7]=2)=[CH:13][CH:12]=1

Komponenten

4

Edukt 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 5995285-Bromo-2-hydroxypyridine

Produkt 1

HCID 200814975-(4-Methoxyphenyl)pyridin-2(1H)-oneAusbeute 69,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21867204Cyclohexane ethylacetateLösungsmittel

Versuchsvorschrift

According to Scheme 5 Step 1: The title compound was prepared from 5-bromopyridin-2(1H)-one (1 eq, 17.2 mmol, 3.00 g, Example 1 Step 1) and 4-methoxyphenylboronic acid (1.5 eq, 25.9 mmol, 3.93 g) according to the procedure described for Example 2 Step 2. Reaction conditions: 4.5 hours at 120° C. The crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 70 g SiO2) using pure AcOEt then AcOEt/MeOH 95/5 as eluent to afford 5-(4-methoxyphenyl)-(1H)-pyridin-2-one (11.9 mmol, 2.40 g, 69%) as a white solid.

Aufarbeitung

  1. customReaction conditions
  2. custom4.5 hours
  3. customat 120° C
  4. customThe crude product was purified by flash chromatography over silica gel (AIT Flashsmart prepacked column 70 g SiO2)

Quellen und Nachweise

ORD-Eintrag
ord-873d2377f0a74c83b8b30ac49b0d599f
Quelldatensatz
uspto-grants-2013_03
Patentnummer
US08399493B2

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