Water → 2-Butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methylamino)isoindolin-1-one

HRID 1182706

Reaktionsgleichung

Reaktionsgleichung von HRID 1182706
[NH2:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[N:6]([CH2:12][CH2:13][CH2:14][CH3:15])[CH2:5]2.C([O-])([O-])=O.[K+].[K+].CS(O[CH2:27][C:28]1[C:29]([CH3:41])=[N:30][C:31]([CH3:40])=[CH:32][C:33]=1[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)(=O)=O.O>CN(C=O)C>[CH2:12]([N:6]1[CH2:5][C:4]2[C:8](=[CH:9][CH:10]=[C:2]([NH:1][CH2:27][C:28]3[C:29]([CH3:41])=[N:30][C:31]([CH3:40])=[CH:32][C:33]=3[C:34]3[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=3)[CH:3]=2)[C:7]1=[O:11])[CH2:13][CH2:14][CH3:15]

Komponenten

6

Edukt 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 674320655-Amino-2-butyl-2,3-dihydro-1H-isoindol-1-oneHCID 86658032(2,6-Dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate

Produkt 1

HCID 674343322-Butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methylamino)isoindolin-1-oneAusbeute 41,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

5-Amino-2-butylisoindolin-1-one (63.1 mg, 0.309 mmol), K2CO3 (85 mg, 0.618 mmol) and KI (51.3 mg, 0.309 mmol) were added to a solution of (2,6-dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate (90 mg, 0.309 mmol) in DMF (6 mL). After stirring overnight, water was added, the mixture was extracted with EtOAc, the combined organic layers were washed with water and dried (MgSO4). Purification by flash chromatography (DCM/MeOH, gradient 2-8% MeOH) provided 2-butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methylamino)isoindolin-1-one (51 mg, 40%).

Aufarbeitung

  1. extractionthe mixture was extracted with EtOAc
  2. washthe combined organic layers were washed with water
  3. dry with materialdried (MgSO4)
  4. customPurification by flash chromatography (DCM/MeOH, gradient 2-8% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-ba1400901ce04b89b7aa7b68a227d483
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664214B2

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