Pyridine → (R)-3-bromo-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one

HRID 1617783Notes

Reaction equation

HRID 1617783 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH2:9][C:10]([C:12]2[CH:13]=[CH:14][C:15](=[O:19])[N:16]([CH3:18])[CH:17]=2)=[O:11])=[CH:4][CH:3]=1.N1C=CC=CC=1.[Br:33]Br.C(OCC)(=O)C>CN(C=O)C>[Br:33][C:14]1[C:15](=[O:19])[N:16]([CH3:18])[CH:17]=[C:12]([C:10](=[O:11])[CH2:9][C@H:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][CH:6]=2)[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH3:26])[CH:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8857Ethyl AcetateHCID 24408BromineHCID 66668696(R)-5-(3-(4-Bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one

Product 1

HCID 67015677(R)-3-bromo-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-oneYield 78%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (R)-5-(3-(4-bromophenyl)-3-o-tolylpropanoyl)-1-methylpyridin-2(1H)-one (0.1 g, example 223) in DMF (1 mL) were added pyridine (217 μL) and then bromine (12.6 μL) dropwise. The resulting solution was stirred at rt for 2.25 h. The reaction mixture was poured on water and ethyl acetate and the layers were separated. The aqueous layer was extracted with 2× ethyl acetate. The organic layers were washed with water and once with brine, dried over MgSO4, filtered, treated with silica gel and evaporated. The compound was purified by chromatography (SiO2, n-heptane/ethyl acetate 100:0 to 50:50) to give the title compound as a light brown solid (0.093 g; 78%), MS (ESI+): m/z=489.0 [M+H]+.

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted with 2× ethyl acetate
  3. washThe organic layers were washed with water and once with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. additiontreated with silica gel
  7. customevaporated
  8. customThe compound was purified by chromatography (SiO2, n-heptane/ethyl acetate 100:0 to 50:50)

Sources & evidence

ORD record
ord-a3d83545c27243abb2aff2bc3f223148
Source dataset
uspto-grants-2014_07
Patent number
US08765730B2

Reaction notes

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