Bromoacetone → (6-Methoxy-2-methyl-indolizin-1-yl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 273324Notes

Reaction equation

HRID 273324 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][C:10]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[O:11])=[N:7][CH:8]=1.Br[CH2:25][C:26](=O)[CH3:27].C([O-])(O)=O.[Na+]>CC(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:25]=[C:26]([CH3:27])[C:9]=2[C:10]([C:12]2[CH:17]=[C:16]([O:18][CH3:19])[C:15]([O:20][CH3:21])=[C:14]([O:22][CH3:23])[CH:13]=2)=[O:11])[CH:8]=1

Participants

5

Reactant 3

HCID 11715BromoacetoneHCID 516892Sodium BicarbonateHCID 529516172-(5-Methoxypyridin-2-yl)-1-(3,4,5-trimethoxyphenyl)ethanone

Product 1

HCID 52951490(6-Methoxy-2-methyl-indolizin-1-yl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 95%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 2-(5-methoxypyridin-2-yl)-1-(3,4,5-trimethoxyphenyl)ethanone (0.200 g, 0.631 mmol), 1-bromo-2-propanone (0.171 g, 1.3 mmol), and NaHCO3 (0.212 g, 2.6 mmol) in acetone (5 mL) was refluxed for 20 h. The precipitate was removed by filtration. The filtrate was concentrated to give a residue, which was purified on a silica gel column eluting with CH2Cl2 to afford compound 5 (0.213 g, 95%).

Workup

  1. temperaturewas refluxed for 20 h
  2. customThe precipitate was removed by filtration
  3. concentrationThe filtrate was concentrated
  4. customto give a residue, which
  5. customwas purified on a silica gel column
  6. washeluting with CH2Cl2

Sources & evidence

ORD record
ord-a2381464b8864cf18829d39faaf1b9d3
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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