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

HRID 1765356Notes

Reaction equation

HRID 1765356 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% ethyl acetate) 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% ethyl acetate)

Sources & evidence

ORD record
ord-81299beceee74fbb98c3b11d18ee5e41
Source dataset
uspto-grants-2007_06
Patent number
US07226923B2

Reaction notes

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