Methyl iodide → 4-Bromo-2-isopropyl-7-methoxymethyl-2H-phthalazin-1-one

HRID 1783670Notes

Reaction equation

HRID 1783670 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][OH:13])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1.[H-].[Na+].[CH3:20]I>C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([CH2:12][O:13][CH3:20])=[CH:9][CH:10]=2)[C:5](=[O:14])[N:4]([CH:15]([CH3:17])[CH3:16])[N:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21106569HCID 21106569, compound

Product 1

HCID 211065634-Bromo-2-isopropyl-7-methoxymethyl-2H-phthalazin-1-oneYield 69.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

4-Bromo-7-hydroxymethyl-2-isopropyl-2H-phthalazin-1-one (0.11 g, 0.37 mmol) was dissolved in THF (2 ml). To this was added NaH (60%, 0.019 g, 0.44 mmol) as a THF suspension (2 ml). To this was added methyl iodide (0.063 g, 0.48 mmol) and the reaction mixture was stirred for 20 hours. The reaction mixture was concentrated under vacuum and the residue was purified by flash column chromatography (elution: 80% heptane, 20% EtOAc) to give the title compound (0.08 g, 69% yield) as a white solid.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum
  2. customthe residue was purified by flash column chromatography (elution: 80% heptane, 20% EtOAc)

Sources & evidence

ORD record
ord-b4c14feb9c614272842705abd1c6a541
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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