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

HRID 1783662Notes

Reaction equation

HRID 1783662 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>C1COCC1>[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-mercap-to-2-isopropyl-4-bromo-2H-phthalazin-1-one (0.77 g, 2.6 mmol) in THF (8 ml), was added NaH (60%, 0.13 g, 3.1 mmol) portion-wise. After stirring for 5 min, 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% EtOAc) to give the title compound (0.44 g, 54% yield) as a white solid. 1H-NMR: (400 MHz, D6-DMSO), 8.02 (1H, d), 7.88 (1H, d), 7.75 (1 H, d), 5.26-5.15 (1H, m), 2.59 (3H, s), 1.35 (6H, d).

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% EtOAc)

Sources & evidence

ORD record
ord-e5a6c44deaa44f9d8c92aa3671b9df28
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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