Cesium carbonate → 3-tert-butyl-2-methyl-4-phenyl-6-(4-phenylbutoxy)isoquinolin-1(2H)-one

HRID 2196390Notes

Reaction equation

HRID 2196390 reaction equation
[C:1]([C:5]1[N:6]([CH3:23])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[CH:12][C:11]([OH:21])=[CH:10][CH:9]=2)([CH3:4])([CH3:3])[CH3:2].[C:24]1([CH2:30][CH2:31][CH2:32][CH2:33]I)[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[C:1]([C:5]1[N:6]([CH3:23])[C:7](=[O:22])[C:8]2[C:13]([C:14]=1[C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[CH:12][C:11]([O:21][CH2:33][CH2:32][CH2:31][CH2:30][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)=[CH:10][CH:9]=2)([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 112782303-tert-butyl-6-hydroxy-2-methyl-4-phenylisoquinolin-1(2H)-oneHCID 12709818(4-Iodobutyl)benzene

Product 1

HCID 113166023-tert-butyl-2-methyl-4-phenyl-6-(4-phenylbutoxy)isoquinolin-1(2H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-tert-butyl-6-hydroxy-2-methyl-4-phenylisoquinolin-1(2H)-one (50 mg), 4-phenyl-1-iodobutane (100 mg) and cesium carbonate (100 mg) in DMF (2.5 mL) was heated at 80 C for 6 h. The reaction was partitioned between water and EtOAc. The organic solution was dried (Na2SO4) and concentrated, then purified by flash chromatography (20% EtOAc in hexanes) to give the titled compound.

Workup

  1. customThe reaction was partitioned between water and EtOAc
  2. dry with materialThe organic solution was dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified by flash chromatography (20% EtOAc in hexanes)

Sources & evidence

ORD record
ord-ecefeb6c2a434cebba8617c2056bd188
Source dataset
uspto-grants-2012_12
Patent number
US08338449B2

Reaction notes

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