1-Bromo-2-butanone → (2-Ethyl-6-methoxy-indolizin-1-yl)-(3,4,5-trimethoxy-phenyl)-methanone

HRID 273325Notes

Reaction equation

HRID 273325 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)[CH2:27][CH3:28].C([O-])(O)=O.[Na+]>CC(C)=O>[CH2:27]([C:26]1[C: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])=[C:6]2[N:7]([CH:25]=1)[CH:8]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5]2)[CH3:28]

Participants

5

Reactant 3

HCID 131561-Bromo-2-butanoneHCID 516892Sodium BicarbonateHCID 529516172-(5-Methoxypyridin-2-yl)-1-(3,4,5-trimethoxyphenyl)ethanone

Product 1

HCID 58668402(2-Ethyl-6-methoxy-indolizin-1-yl)-(3,4,5-trimethoxy-phenyl)-methanoneYield 92%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of A mixture of 2-(5-methoxypyridin-2-yl)-1-(3,4,5-trimethoxyphenyl)ethanone (0.200 g, 0.631 mmol), 1-bromo-2-butanone (0.190 g, 1.3 mmol), and NaHCO3 (0.212 g, 2.6 mmol) in acetone (5 mL) was heated under reflux 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 6 (0.213 g, 92%).

Workup

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

Sources & evidence

ORD record
ord-88d564d9a8734c28b6c883872d6efa80
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Reaction notes

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