Dimethyl Sulfoxide → 2-(3-Bromo-phenyl)-6-dimethylamino-3,4-dihydro-2H-isoquinolin-1-one

HRID 2069740Notes

Reaction equation

HRID 2069740 reaction equation
[CH3:1][N:2]([CH3:14])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[C:9](=[O:13])[NH:8][CH2:7][CH2:6]2.C(=O)([O-])[O-].[K+].[K+].CS(C)=O.[Br:25][C:26]1[CH:31]=[CH:30][CH:29]=[C:28](Br)[CH:27]=1>ClCCl>[Br:25][C:26]1[CH:27]=[C:28]([N:8]2[CH2:7][CH2:6][C:5]3[C:10](=[CH:11][CH:12]=[C:3]([N:2]([CH3:14])[CH3:1])[CH:4]=3)[C:9]2=[O:13])[CH:29]=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 79271,3-DibromobenzeneHCID 11430Potassium CarbonateHCID 574241216-(Dimethylamino)-3,4-dihydroisoquinolin-1(2H)-one

Product 1

HCID 592163952-(3-Bromo-phenyl)-6-dimethylamino-3,4-dihydro-2H-isoquinolin-1-oneYield 67.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
150 °C

Procedure

6-Dimethylamino-3,4-dihydro-2H-isoquinolin-1-one (762 mg, 4.01 mmol), cuprous iodide (153mg, 0.802 mmol) and potassium carbonate (554 mg, 4.01 mmol) were deposited in a sealed type vessel. 6 mL DMSO and 1,3-dibromobenzene (1.89 g, 8.01 mmol) were added. Argon was bubbled through the mixture for 2 minutes and the lid was tightly closed. This was heated at 150° C. for 24 hours. Cuprous iodide (153 mg, 0.802 mmol) was added and the mixture was heated at 150° C. for an additional 24 hours. This was diluted with dichoromethane and filtered through a pad of celite. The filtrate was partitioned between dichloromethane and 5% aq. ammonium hydroxide. The dichloromethane layer was dried over anhydrous magnesium sulfate, concentrated in vacuo, and purified by flash chromatography (gradient elution 25 to 100% ethyl acetate/hexanes) to yield 2-(3-Bromo-phenyl)-6-dimethylamino-3,4-dihydro-2H-isoquinolin-1-one (939 mg, 2.72 mmol). MS (ESI) 345.0 (M+H)+.

Workup

  1. customArgon was bubbled through the mixture for 2 minutes
  2. customthe lid was tightly closed
  3. temperaturethe mixture was heated at 150° C. for an additional 24 hours
  4. filtrationfiltered through a pad of celite
  5. customThe filtrate was partitioned between dichloromethane and 5% aq. ammonium hydroxide
  6. dry with materialThe dichloromethane layer was dried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. custompurified by flash chromatography (gradient elution 25 to 100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-414dbbcabab84849860c8f15a06023ee
Source dataset
uspto-grants-2012_10
Patent number
US08299077B2

Reaction notes

Loading…