Methyl iodide → 7-Methylsulfanyl-2-isopropyl-4-bromo-2H-phthalazin-1-one

HRID 1765348Notes

Reaction equation

HRID 1765348 reaction equation
[SH: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.[H-].[Na+].[CH3:19]I>O1CCCC1>[CH3:19][S:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]([Br:16])=[N:7][N:8]([CH:13]([CH3:14])[CH3:15])[C:9]2=[O:12])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 1363729987-Mercapto-2-isopropyl-4-bromo-2H-phthalazin-1-one

Product 1

HCID 211065857-Methylsulfanyl-2-isopropyl-4-bromo-2H-phthalazin-1-oneYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-Mercapto-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.77 g, 2.6 mmol) in tetrahydrofuran (THF) (8 ml), was added NaH (60%, 0.13 g, 3.1 mmol) portion-wise. After stirring for five minutes, methyl iodide (0.44 g, 3.1 mmol) was added dropwise and stirring was continued for four hours. The mixture was concentrated under vacuum and the residue was subjected to flash column chromatography (elution: 90% heptane, 10% ethyl acetate) to give the title compound (0.44 g, 54% yield) as a white solid.

Workup

  1. stirringstirring
  2. waitwas continued for four hours
  3. concentrationThe mixture was concentrated under vacuum
  4. washthe residue was subjected to flash column chromatography (elution: 90% heptane, 10% ethyl acetate)

Sources & evidence

ORD record
ord-51308b2ba9cb46c89bf12f488347e741
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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