3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one → 5-Biphenyl-3-yl-3-hydroxy-1-methylpyridin-2(1H)-one

HRID 625941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 625941
C([O:8][C:9]1[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=[C:13]([C:15]2[CH:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:18]=[CH:19][CH:20]=2)[CH:14]=1)C1C=CC=CC=1>CO.[Pd]>[C:17]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=[C:15]([C:13]2[CH:14]=[C:9]([OH:8])[C:10](=[O:28])[N:11]([CH3:27])[CH:12]=2)[CH:16]=1

Komponenten

4

Edukt 1

HCID 674189793-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one

Produkt 1

HCID 533798115-Biphenyl-3-yl-3-hydroxy-1-methylpyridin-2(1H)-oneAusbeute 10 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

A solution of 3-(benzyloxy)-5-(biphenyl-3-yl)-1-methylpyridin-2(1H)-one (34 mg, 0.093 mmol) in MeOH (5 mL) was hydrogenated under atmospheric H2 in the presence of 5% Pd/C (15 mg) for 21 h. Filtered and concentrated. Purification by preparative HPLC (5-65% CH3CN/H2O over 20 min, 0.05% added TFA) afforded 2.5 mg (10%) of 5-Biphenyl-3-yl-3-hydroxy-1-methylpyridin-2(1H)-one as a white solid. 1H NMR (500 MHz, CDCl3): δ 7.63-7.60 (m, 3H), 7.56 (d, J=7.8 Hz, 1H), 7.52-7.43 (m, 3H), 7.41-7.36 (m, 2H), 7.25-7.06 (br, 2H), 3.72 (s, 3H). High resolution mass spec (FT/ICR) cale (M+H)+=278.1165 found 278.1176.

Aufarbeitung

  1. filtrationFiltered
  2. concentrationconcentrated
  3. customPurification
  4. additionby preparative HPLC (5-65% CH3CN/H2O over 20 min, 0.05% added TFA)

Quellen und Nachweise

ORD-Eintrag
ord-b76c338679c74cadb8df6cd184d19aae
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309199B2

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