2,3-Dichloropropene → Methyl 2-[N-(5-bromo-2-(2-chloroallyloxy)benzyl)-N-ethylamino]-5-pyridyl-carboxylate

HRID 1870751Notes

Reaction equation

HRID 1870751 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([OH:21])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10].[C:22]([O-])([O-])=O.[K+].[K+].[Cl:28][C:29]([CH2:31]Cl)=[CH2:30]>CN(C=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([O:21][CH2:31][C:29]([Cl:28])=[CH2:30])=[C:6]([CH:20]=1)[CH2:7][N:8]([C:11]1[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:22])=[O:18])=[CH:13][N:12]=1)[CH2:9][CH3:10]

Participants

5

Reactant 3

HCID 65652,3-DichloropropeneHCID 11430Potassium CarbonateHCID 226225362-[N-(5-Bromo-2-hydroxybenzyl)-N-ethylamino]pyridine-5-carboxylic Acid

Product 1

HCID 11102232Methyl 2-[N-(5-bromo-2-(2-chloroallyloxy)benzyl)-N-ethylamino]-5-pyridyl-carboxylateYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of methyl 2-[N-(5-bromo-2-hydroxybenzyl)-N-ethylamino]-5-pyridylcarboxylate (reference example 7) (0.73 g, 2 mM) in DMF (12 ml) was treated with K2CO3 (0.83 g, 6 mM) and 2,3-dichloro-1-propene (0.490 g, 44 mM). The reaction was allowed to stir at ambient temperature for 48 hours. The reaction was evaporated at reduced pressure. The residue was subjected to chromatography (eluant: ethyl acetate/hexane) to give the title compound as a white solid (0.8 g).

Workup

  1. customThe reaction was evaporated at reduced pressure

Sources & evidence

ORD record
ord-01d968de8b564c1ea41c9e3ce58fba03
Source dataset
uspto-grants-2000_08
Patent number
US06100258

Reaction notes

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