Potassium Carbonate → 1-(4-(methylsulfonyl)phenyl)-4-(1-(5-(prop-1-en-2-yl)pyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-one

HRID 1518443

Reaktionsgleichung

Reaktionsgleichung von HRID 1518443
Br[C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][CH:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]([C:21]4[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=4)[C:17](=[O:31])[CH:16]=3)[CH2:10][CH2:9]2)=[N:6][CH:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:38]=[C:39](B(O)O)[CH3:40]>CN(C=O)C.O>[CH3:30][S:27]([C:24]1[CH:25]=[CH:26][C:21]([N:18]2[CH:19]=[CH:20][C:15]([O:14][CH:11]3[CH2:12][CH2:13][N:8]([C:5]4[N:4]=[CH:3][C:2]([C:39]([CH3:40])=[CH2:38])=[CH:7][N:6]=4)[CH2:9][CH2:10]3)=[CH:16][C:17]2=[O:31])=[CH:22][CH:23]=1)(=[O:29])=[O:28]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 10855372(Prop-1-en-2-yl)boronic acidHCID 252046474-(1-(5-bromopyrimidin-2-yl)piperidin-4-yloxy)-1-(4-(methylsulfonyl)phenyl)pyridin-2(1H)-one

Produkt 1

HCID 673661321-(4-(methylsulfonyl)phenyl)-4-(1-(5-(prop-1-en-2-yl)pyrimidin-2-yl)piperidin-4-yloxy)pyridin-2(1H)-oneAusbeute 26,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

A mixture of 4-(1-(5-bromopyrimidin-2-yl)piperidin-4-yloxy)-1-(4-(methylsulfonyl)phenyl)pyridin-2(1H)-one (103 mg, 0.20 mmol), potassium carbonate (140 mg, 1.02 mmol, EMD) and prop-1-en-2-ylboronic acid (52.4 mg, 0.610 mmol) in DMF (1.8 mL) and Water (0.2 mL) was degassed by vacuum and purged with Argon. To the resulting mixture was added 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (16.72 mg, 0.020 mmol, Aldrich) and then heated under microwave conditions at 120° C. for 20 min. The reaction mixture was concentrated in vacuo to a brown solid. The solid was purified by flash chromatography (SiO2, 0 to 100% EtOAc in hexanes) to yield 25 mg of desired product as a light yellow solid. MS (ESI) 467 (M+H).

Aufarbeitung

  1. customwas degassed by vacuum
  2. custompurged with Argon
  3. additionTo the resulting mixture was added 1,1′-Bis(diphenylphosphino)ferrocene-palladium(II) dichloride dichloromethane complex (16.72 mg, 0.020 mmol, Aldrich)
  4. concentrationThe reaction mixture was concentrated in vacuo to a brown solid
  5. customThe solid was purified by flash chromatography (SiO2, 0 to 100% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-f798f90fc4324413a7985db39376f867
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08232404B2

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