2-(Phenylmethyl)pyridine → 2-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizine

HRID 1963043Notes

Reaction equation

HRID 1963043 reaction equation
Br[CH2:2][C:3](=O)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=1[CH3:12].[CH2:14]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][N:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CC(C)=O>[F:11][C:7]1[C:6]([CH3:12])=[C:5]([CH:10]=[CH:9][CH:8]=1)[CH2:4][C:3]1[C:14]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[C:21]2[N:22]([CH:2]=1)[CH:23]=[CH:24][CH:25]=[CH:26]2

Participants

4

Reactant 2

HCID 75812-(Phenylmethyl)pyridineHCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

Product 1

HCID 677730242-(3-Fluoro-2-methyl-benzyl)-1-phenyl-indolizineYield 33.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound of step 2 (1.50 g, 6.12 mmol) and 2-benzyl-pyridine (2.071 g, 12.24 mmol) were dissolved in acetone (30 ml) and the mixture was stirred under reflux overnight. The mixture was concentrated to dryness and the residue was purified by chromatography on silica gel (cyclohexane) to give 0.653 g of the title compound.

Workup

  1. temperatureunder reflux overnight
  2. concentrationThe mixture was concentrated to dryness
  3. customthe residue was purified by chromatography on silica gel (cyclohexane)

Sources & evidence

ORD record
ord-a857ff382b0a4e8abaa8d4ebf918fd2d
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

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