Methanol → HCID 68431773, compound

HRID 15049Notes

Reaction equation

HRID 15049 reaction equation
O1CCCC1.Br[C:7]1[C:8](=[O:35])[N:9]([C:22]2[CH:27]=[CH:26][C:25]([O:28][CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][O:30]3)=[CH:24][CH:23]=2)[N:10]=[CH:11][C:12]=1[O:13][CH2:14][C:15]1[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=1.CCCCCC.C([Li])CCC.CO>C(OCC)(=O)C>[F:21][C:18]1[CH:17]=[CH:16][C:15]([CH2:14][O:13][C:12]2[CH:11]=[N:10][N:9]([C:22]3[CH:23]=[CH:24][C:25]([O:28][CH:29]4[CH2:34][CH2:33][CH2:32][CH2:31][O:30]4)=[CH:26][CH:27]=3)[C:8](=[O:35])[CH:7]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 68431211HCID 68431211, compoundHCID 178418244HCID 178418244, compound

Product 1

HCID 68431773HCID 68431773, compoundYield 65.3%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a tetrahydrofuran solution (1 mL) of 4-bromo-5-(4-fluorobenzyloxy)-2-{4-[(2-tetrahydropyranyl)oxy]phenyl}-2H-pyridazin-3-one (136 mg, 0.29 mmol), 2.66 N n-butyl lithium hexane-solution (0.13 mL, 0.35 mmol) was added at −78° C. and stirred for 30 minutes. Methanol was added to the reaction liquid, warmed up to room temperature and ethyl acetate was added. Thus obtained organic layer was washed with 5% aqueous citric acid solution and saturated brine, and dried over anhydrous magnesium sulfate. Concentrating the solvent under reduced pressure, the resulting residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:1) to provide the title compound (74.2 mg, 65.3%).

Workup

  1. washThus obtained organic layer was washed with 5% aqueous citric acid solution and saturated brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. concentrationConcentrating the solvent under reduced pressure
  4. customthe resulting residue was purified on silica gel column chromatography (C-300; ethyl acetate:hexane=1:1)

Sources & evidence

ORD record
ord-a95beb4a5b7941b19ff063adf4e3bc26
Source dataset
uspto-grants-2010_06
Patent number
US07732456B2

Reaction notes

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