Sodium hydride → 4-Bromo-7-cyclopropylmethoxymethyl-2-isopropyl-2H-phthalazin-1-one

HRID 1783725Notes

Reaction equation

HRID 1783725 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].[Br:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19]Br)=[CH:16][CH:17]=2)[C:12](=[O:21])[N:11]([CH:22]([CH3:24])[CH3:23])[N:10]=1>C1COCC1>[Br:8][C:9]1[C:18]2[C:13](=[CH:14][C:15]([CH2:19][O:5][CH2:4][CH:1]3[CH2:3][CH2:2]3)=[CH:16][CH:17]=2)[C:12](=[O:21])[N:11]([CH:22]([CH3:24])[CH3:23])[N:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 75644CyclopropanemethanolHCID 211065684-Bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one

Product 1

HCID 689811124-Bromo-7-cyclopropylmethoxymethyl-2-isopropyl-2H-phthalazin-1-oneYield 87%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Cyclopropyl-methanol (0.05 ml, 0.67 mmol) was dissolved in THF (1 ml). To this was added NaH (60%, 0.028 g, 0.72 mmol) in a single portion. The mixture was stirred at RT for 5 min then 4-bromo-7-bromomethyl-2-isopropyl-2H-phthalazin-1-one (0.2 g, 0.56 mmol) in THF (1 ml) was added in one portion and the reaction mixture was stirred for 1 hour. Whereupon LC-MS indicated complete consumption of starting material, the solvent was removed under vacuum and the residue was purified by flash column chromatography (elution: 80% heptane, 20% EtOAc) to give the title compound (0.17 g, 87% yield) as a light yellow oil. Tr=1.80 min, m/z (ES+) (M+H)+ 351 & 353

Workup

  1. stirringthe reaction mixture was stirred for 1 hour
  2. customconsumption of starting material
  3. customthe solvent was removed under vacuum
  4. customthe residue was purified by flash column chromatography (elution: 80% heptane, 20% EtOAc)

Sources & evidence

ORD record
ord-eb4446fd96b64ba993f7f75bb602bcb5
Source dataset
uspto-grants-2009_03
Patent number
US07501410B2

Reaction notes

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