Potassium Carbonate → 2-Butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methoxy)isoindolin-1-one

HRID 1182705Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1182705
[CH2:1]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([OH:14])[CH:11]=2)[C:6]1=[O:15])[CH2:2][CH2:3][CH3:4].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.[OH-].[Na+]>CN(C=O)C.O>[CH2:1]([N:5]1[CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[C:10]([O:14][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:11]=2)[C:6]1=[O:15])[CH2:2][CH2:3][CH3:4]

Komponenten

7

Edukt 4

HCID 11430Potassium CarbonateHCID 14798Sodium HydroxideHCID 138973842-Butyl-5-hydroxyisoindolin-1-oneHCID 86658032(2,6-Dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate

Produkt 1

HCID 533855942-Butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methoxy)isoindolin-1-oneAusbeute 19,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2-Butyl-5-hydroxyisoindolin-1-one (366 mg, 1.78 mmol), K2CO3 (493 mg, 3.57 mmol) and KI (296 mg, 1.78 mmol) were added to a solution of (2,6-dimethyl-4-phenylpyridin-3-yl)methyl methanesulfonate (520 mg, 1.78 mmol) in DMF (18 mL). After stirring overnight at room temperature (rt), water was added and the pH was adjusted to 13-14 using aqueous NaOH (1 M). The reaction mixture was extracted with EtOAc, the combined organic layers were washed with water, dried with MgSO4 and the solvent was removed in vacuo. Purification by flash chromatography (DCM/MeOH, gradient 1-5% MeOH) provided 2-butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methoxy)isoindolin-1-one (140 mg, 19%). ESI-MS [M+H]+=401.2.

Aufarbeitung

  1. additionwas added
  2. extractionThe reaction mixture was extracted with EtOAc
  3. washthe combined organic layers were washed with water
  4. dry with materialdried with MgSO4
  5. customthe solvent was removed in vacuo
  6. customPurification by flash chromatography (DCM/MeOH, gradient 1-5% MeOH)

Quellen und Nachweise

ORD-Eintrag
ord-978a909e9d234bf69e6dc4e4bb57ef7b
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08664214B2

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