Methyl 2-pyridylacetate → 2-(3-Fluoro-2-methyl-benzyl)indolizine-1-carboxylic acid methyl ester

HRID 1963091Notes

Reaction equation

HRID 1963091 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].[CH3:14][O:15][C:16](=[O:24])[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1.C(=O)([O-])O.[Na+]>CC(=O)CC>[CH3:14][O:15][C:16]([C:17]1[C:3]([CH2:4][C:5]2[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[C:6]=2[CH3:12])=[CH:2][N:19]2[C:18]=1[CH:23]=[CH:22][CH:21]=[CH:20]2)=[O:24]

Participants

5

Reactant 3

HCID 74264Methyl 2-pyridylacetateHCID 516892Sodium BicarbonateHCID 866706671-Bromo-3-(3-fluoro-2-methyl-phenyl)-propan-2-one

Product 1

HCID 677725592-(3-Fluoro-2-methyl-benzyl)indolizine-1-carboxylic acid methyl esterYield 61.3%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

The compound of step 1 (3.89 g, 15.88 mmol), pyridin-2-ylacetic acid methyl ester (1.65 g, 10.92 mmol) and sodium hydrogencarbonate (4.59 g, 54.60 mmol) in butan-2-one (43 ml) were heated under reflux for 24 h. The solid was removed by filtration and the filtrate was concentrated. The residue was purified by silica gel chromatography (HEP/EA) to give 1.99 g of the title compound.

Workup

  1. temperatureunder reflux for 24 h
  2. customThe solid was removed by filtration
  3. concentrationthe filtrate was concentrated
  4. customThe residue was purified by silica gel chromatography (HEP/EA)

Sources & evidence

ORD record
ord-e3dcd27bd7a74630a1a0df74d7f12153
Source dataset
uspto-grants-2013_04
Patent number
US08415336B2

Reaction notes

Loading…