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

HRID 1182706Notes

Reaction equation

HRID 1182706 reaction equation
[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]

Participants

6

Reactant 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

Product 1

HCID 674343322-Butyl-5-((2,6-dimethyl-4-phenylpyridin-3-yl)methylamino)isoindolin-1-oneYield 41.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-ba1400901ce04b89b7aa7b68a227d483
Source dataset
uspto-grants-2014_03
Patent number
US08664214B2

Reaction notes

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