Dimethylformamide → 6-Bromo-2-(4-methanesulfonyl-benzyl)-2H-isoquinolin-1-one

HRID 907332Notes

Reaction equation

HRID 907332 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[NH:7][CH:6]=[CH:5]2.C(=O)([O-])[O-].[K+].[K+].Cl[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:23][CH:22]=1.CN(C=O)C>O>[Br:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[N:7]([CH2:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([CH3:30])(=[O:29])=[O:28])=[CH:25][CH:26]=1)[CH:6]=[CH:5]2

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 1235301-(Chloromethyl)-4-methanesulfonylbenzeneHCID 158851826-Bromoisoquinolin-1(2H)-one

Product 1

HCID 575517876-Bromo-2-(4-methanesulfonyl-benzyl)-2H-isoquinolin-1-oneYield 38.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of intermediate 1 (3.0 g), potassium carbonate (3.70 g), 1-(chloromethyl)-4-(methylsulfonyl)benzene (2.74 g) and DMF (20 mL) was heated at 50° C. for 24 hours. The mixture was allowed to cool then poured into water (50 mL) and extracted with dichloromethane (100 mL). The extracts were combined, evaporated under reduced pressure and the residue purified (SiO2 chromatography, eluting with 2% methanol in dichloromethane) to give the sub-titled compound (2.0 g).

Workup

  1. temperatureto cool
  2. extractionextracted with dichloromethane (100 mL)
  3. customevaporated under reduced pressure
  4. customthe residue purified
  5. wash(SiO2 chromatography, eluting with 2% methanol in dichloromethane)

Sources & evidence

ORD record
ord-735423a92e90402b9064afcdcb7a529c
Source dataset
uspto-grants-2011_09
Patent number
US08012979B2

Reaction notes

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