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

HRID 2240199Notes

Reaction equation

HRID 2240199 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-ad5718845b254c28a2f879b52869cf95
Source dataset
uspto-grants-2010_05
Patent number
US07723352B2

Reaction notes

Loading…