2-Chloroethyl methyl sulfide → 4-Bromo-2-isopropyl-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-one

HRID 1783711Notes

Reaction equation

HRID 1783711 reaction equation
[OH:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:15])[CH3:14])[C:9]2=[O:12])=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH3:23][S:24][CH2:25][CH2:26]Cl>CN(C=O)C>[Br:16][C:6]1[C:5]2[C:10](=[CH:11][C:2]([O:1][CH2:26][CH2:25][S:24][CH3:23])=[CH:3][CH:4]=2)[C:9](=[O:12])[N:8]([CH:13]([CH3:14])[CH3:15])[N:7]=1

Participants

5

Reactant 3

HCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium CarbonateHCID 1363729927-Hydroxy-2-Isopropyl-4-bromo-2H-phthalazin-1-one

Product 1

HCID 689794224-Bromo-2-isopropyl-7-(2-methylsulfanyl-ethoxy)-2H-phthalazin-1-oneYield 30%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 7-hydroxy-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.8 g, 0.0028 mol) in DMF (8 ml), was added potassium carbonate (2 g, 0.014 mol). After 5 min, 2-chloroethyl methyl sulfide (0.34 g, 0.0028 mol) was added and the solution was heated to 100° C. for 24 hours. After this time LC-MS indicated the complete consumption of starting material and the mixture was cooled, concentrated under vacuum and purified by flash column chromatography (elution: 70% heptane, 30% EtOAc) to give the title compound (0.3 g, 24% yield) as a white solid.

Workup

  1. customthe complete consumption of starting material
  2. temperaturethe mixture was cooled
  3. concentrationconcentrated under vacuum
  4. custompurified by flash column chromatography (elution: 70% heptane, 30% EtOAc)

Sources & evidence

ORD record
ord-5068cdcca80b424da091e6122b654003
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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