Bromoacetone → 7-Methoxy-2-methylindolizine

HRID 273327

Reaction equation

HRID 273327 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([CH3:9])[CH:4]=1.Br[CH2:11][C:12](=O)[CH3:13].N12CCCN=C1CCCCC2>C1C=CC=CC=1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][N:6]2[C:5]([CH:4]=1)=[CH:9][C:12]([CH3:13])=[CH:11]2

Participants

5

Reactant 3

HCID 11715BromoacetoneHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 47377584-Methoxy-2-methylpyridine

Product 1

HCID 529516187-Methoxy-2-methylindolizineYield 31%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

4-Methoxy-2-methylpyridine (0.123 g, 1 mmol) and bromoacetone (0.16 mL, 1 mmol) were heated at 95° C. under N2 for 2 h. 1,8-Diazabicyclo-[5.4.0]-undec-7-ene (0.34 mL, 2.2 mmol) in benzene (10 mL) was added. The mixture was then refluxed under N2 for 1 h, poured into ice water, and then extracted with EtOAc. The combined organic layers were washed with water and dried. After the solvent was removed in vacuo, the residue was purified on a silica gel column eluting with EtOAc:Hexane (1:9) and EtOAc to give 7-methoxy-2-methylindolizine (0.050 g, 31%).

Workup

  1. temperatureThe mixture was then refluxed under N2 for 1 h
  2. extractionextracted with EtOAc
  3. washThe combined organic layers were washed with water
  4. customdried
  5. customAfter the solvent was removed in vacuo
  6. customthe residue was purified on a silica gel column
  7. washeluting with EtOAc:Hexane (1:9) and EtOAc

Sources & evidence

ORD record
ord-6df95fb68b7c47248a73d1d03ad07ace
Source dataset
uspto-grants-2008_11
Patent number
US07456289B2

Linked notes

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