2-Bromo-2'-nitroacetophenone → Methyl-2-(2-nitrophenyl)indolizine-1-carboxylate

HRID 930794Notes

Reaction equation

HRID 930794 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[N+:11]([O-:13])=[O:12])=O.[N:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH2:20][C:21]([O-:23])=[O:22].[C:24]([O-])(O)=O.[Na+]>CC(C)=O>[CH3:24][O:22][C:21]([C:20]1[C:3]([C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[N+:11]([O-:13])=[O:12])=[CH:2][N:14]2[C:15]=1[CH:16]=[CH:17][CH:18]=[CH:19]2)=[O:23]

Participants

5

Reactant 3

HCID 2440252-Bromo-2'-nitroacetophenoneHCID 516892Sodium BicarbonateHCID 69315582-Pyridylacetate

Product 1

HCID 118970843Methyl-2-(2-nitrophenyl)indolizine-1-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

First, 2.2 mmol of 2-bromo-2′-nitroacetophenone, 3.3. mmol (1.5 eq.) of 2-pyridylacetate and 4.4 mmol (2 eq.) of NaHCO3 are dissolved into 10 ml of acetone and the reaction mixture is allowed to react at 90° C. for 16 hours. After the completion of the reaction, the reaction mixture is concentrated under reduced pressure, dissolved into 10 ml of dichloromethane, and washed with 10 ml of water to remove impurities. Then, 10 ml of dichloromethane is added to the aqueous layer to carry out extraction once more. The resultant organic layer is dried over magnesium sulfate, concentrated under reduced pressure, and purified by silica gel column chromatography using hexane:ethyl acetate:dichloromethane=10:1:2 as a solvent to obtain the target compound.

Workup

  1. customto react at 90° C. for 16 hours
  2. customAfter the completion of the reaction
  3. concentrationthe reaction mixture is concentrated under reduced pressure
  4. dissolutiondissolved into 10 ml of dichloromethane
  5. washwashed with 10 ml of water
  6. customto remove impurities
  7. additionThen, 10 ml of dichloromethane is added to the aqueous layer
  8. extractionextraction once more
  9. dry with materialThe resultant organic layer is dried over magnesium sulfate
  10. concentrationconcentrated under reduced pressure
  11. custompurified by silica gel column chromatography
  12. customethyl acetate:dichloromethane=10:1:2 as a solvent to obtain the target compound

Sources & evidence

ORD record
ord-3b49bfd4ea944b1fa43926147627c42e
Source dataset
uspto-grants-2016_03
Patent number
US09296751B1

Reaction notes

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