Methyl iodide → (S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)-2-methylpyridazin-3(2H)-one

HRID 1527974Notes

Reaction equation

HRID 1527974 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[C:13](=[O:18])[NH:14][N:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1.IC.[C:28](=O)([O-])[O-].[K+].[K+]>CN(C)C(=O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[CH3:25])[CH2:9][C:10]([C:12]2[C:13](=[O:18])[N:14]([CH3:28])[N:15]=[CH:16][CH:17]=2)=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 86684801(S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-one

Product 1

HCID 86684802(S)-4-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)-2-methylpyridazin-3(2H)-oneYield 90%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of (S)-4-(3-(4-bromophenyl)-3-o-tolylpropanoyl)pyridazin-3(2H)-one (293 mg, 679 μmol) in N,N-dimethylacetamide (4 mL) was added iodomethane (101 mg, 712 μmol) followed by potassium carbonate (103 mg, 746 μmol). The reaction mixture was stirred for 5½ h at room temperature and then partitioned between water and ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered, and evaporated. Chromatography (SiO2, gradient heptane to heptane/ethyl acetate 1:1) produced the title compound (251 mg, 90%). White solid, MS: 411.2 [M+H]+.

Workup

  1. custompartitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-e9ce86776b5b44fdb9ce84b24caee9cd
Source dataset
uspto-grants-2015_07
Patent number
US09090565B2

Reaction notes

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