Sodium Carbonate → 1-Cyclohexyl-2-(3-fluoro-2-methyl-benzyl)indolizine

HRID 1963046Notes

Reaction equation

HRID 1963046 reaction equation
[CH:1]1([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[CH2:6][CH2:5][CH2:4][CH:3]=[CH:2]1.Br[CH2:15][C:16](=O)[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=1[CH3:25].C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[CH:1]1([C:7]2[C:16]([CH2:17][C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([F:24])[C:19]=3[CH3:25])=[CH:15][N:9]3[C:8]=2[CH:13]=[CH:12][CH:11]=[CH:10]3)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 677737612-(Cyclohex-2-en-1-ylmethyl)-pyridineHCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

Product 1

HCID 677720901-Cyclohexyl-2-(3-fluoro-2-methyl-benzyl)indolizineYield 64.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound of step 1 (0.415 g, 2.37 mmol) and the compound of step 2 of example 1 (0.58 g, 2.37 mmol) were dissolved in 15 ml of acetone and the solution was stirred under reflux for 36 h. The solution was evaporated to dryness and the solid (0.92 g) dissolved in 10 ml of isopropanol. Sodium carbonate (0.70 g, 6.57 mmol) was added, the mixture was stirred under reflux for 2 h and then evaporated to dryness under reduced pressure. The residue was taken up in DCM and water, and the aqueous phase was extracted twice with DCM. The combined organic phases were dried over sodium sulfate, filtered and evaporated to dryness under reduced pressure. The residue was purified by chromatography on silica gel (HEP/EA, 100:0, then 70:30) to give 0.489 g of the title compound as a thick yellow oil.

Workup

  1. temperatureunder reflux for 36 h
  2. customThe solution was evaporated to dryness
  3. dissolutionthe solid (0.92 g) dissolved in 10 ml of isopropanol
  4. stirringthe mixture was stirred
  5. temperatureunder reflux for 2 h
  6. customevaporated to dryness under reduced pressure
  7. extractionwater, and the aqueous phase was extracted twice with DCM
  8. dry with materialThe combined organic phases were dried over sodium sulfate
  9. filtrationfiltered
  10. customevaporated to dryness under reduced pressure
  11. customThe residue was purified by chromatography on silica gel (HEP/EA, 100:0

Sources & evidence

ORD record
ord-3163b521c22349678360c62b44e8dd8c
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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