Sodium Carbonate → 5-(1-phenyl-1H-1,3-benzodiazol-5-yl)-1-[3-(piperidin-1-yl)propyl]-1,2-dihydropyridin-2-one

HRID 1275552Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1275552
I[C:2]1[CH:3]=[CH:4][C:5](=[O:17])[N:6]([CH2:8][CH2:9][CH2:10][N:11]2[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]2)[CH:7]=1.[C:18]1([N:24]2[C:28]3[CH:29]=[CH:30][C:31](B4OC(C)(C)C(C)(C)O4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O1CCOCC1.O>[C:18]1([N:24]2[C:28]3[CH:29]=[CH:30][C:31]([C:2]4[CH:3]=[CH:4][C:5](=[O:17])[N:6]([CH2:8][CH2:9][CH2:10][N:11]5[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]5)[CH:7]=4)=[CH:32][C:27]=3[N:26]=[CH:25]2)[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Komponenten

7

Edukt 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 120181725-iodo-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-oneHCID 120181731-Phenyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-benzoimidazole

Produkt 1

HCID 53294085-(1-phenyl-1H-1,3-benzodiazol-5-yl)-1-[3-(piperidin-1-yl)propyl]-1,2-dihydropyridin-2-oneAusbeute 71 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 218864351,4-Dioxane--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

5-iodo-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one (18) (0.096 g, 0.28 mmol), 1-phenyl-5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-benzoimidazole (0.081 g, 0.25 mmol), palladium(II) acetate (0.003 g, 0.013 mmol), triphenylphosphine (0.010 g, 0.038 mmol) and sodium carbonate (0,080 g, 0.75 mmol) were stirred in 1.6 mL of a 3:1 mixture of dioxane/water. The mixture was degassed 3x by alternating vacuum and an argon atmosphere. The reaction was heated to 80° C. for 18 h, cooled and diluted with water. The aqueous phase was extracted 3x with EtOAc and the resulting organic phase was dried over Na2SO4, filtered and concentrated. Purification by flash column chromatography (eluted with 85:15 CH2Cl2 /MeOH) afforded 0.073 g 5-(1-phenyl-1H-benzoimidazol-5-yl)-1-(3-piperidin-1-yl-propyl)-1H-pyridin-2-one (19) (71% yield). 1H NMR (CDC13) o 9.60 (s, 1H), 7.90 (d, J=1.3 Hz, 1H), 7.74-7.67 (m, 2H), 7.64-7.48 (m, 6H), 7.39 (dd, J=2.5, 9.5 Hz, 1H), 6.68 (d, J=9.5 Hz, 1H), 4.13 (t, J=6.5 Hz, 2H), 2.42 (bs, 6H), 2.10 (t, J=6.5 Hz, 2H), 1.64 (m, 4H), 1.46 (m, 2H). Mass Spectrometry (for C26H28N4O): [M+H]+413.2334, theoretical 413.2336. ##STR28##

Aufarbeitung

  1. customThe mixture was degassed 3x
  2. temperaturecooled
  3. additiondiluted with water
  4. extractionThe aqueous phase was extracted 3x with EtOAc
  5. dry with materialthe resulting organic phase was dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washby flash column chromatography (eluted with 85:15 CH2Cl2 /MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-0d56e135287f4436afccf9856debe137
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06162804

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