Picolinic acid → Diethyl 2-(5-bromopyridin-2-yl)malonate

HRID 220171

Reaction equation

HRID 220171 reaction equation
[CH2:1]([O:3][C:4](=[O:11])[CH2:5][C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].[Br:12][C:13]1[CH:14]=[CH:15][C:16](I)=[N:17][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].N1C=CC=CC=1C(O)=O>O1CCOCC1.[Cu].[Cu](I)I>[CH2:1]([O:3][C:4](=[O:11])[CH:5]([C:16]1[CH:15]=[CH:14][C:13]([Br:12])=[CH:18][N:17]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2]

Participants

8

Reactant 4

HCID 1018Picolinic acidHCID 7761Diethyl Malonate2×HCID 10796Cesium carbonateHCID 5936905-Bromo-2-iodopyridine

Product 1

HCID 59238270Diethyl 2-(5-bromopyridin-2-yl)malonate

Reagents, catalysts & solvents 3

HCID 23978CopperCatalystHCID 83717Copper iodideCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-(5-Bromo-pyridin-2-yl)-malonic acid diethyl ester (XXXVI) is prepared by copper-catalyzed reaction with malonic acid diethyl ester. The reaction is typically performed by mixing XXXV with malonic acid diethyl ester, copper iodide, cesium carbonate, and pyridine-2-carboxylic acid in 1,4-dioxane and heating to 70 degrees Celsius for 24 hours under nitrogen atmosphere.

Workup

  1. temperatureheating to 70 degrees Celsius for 24 hours under nitrogen atmosphere

Sources & evidence

ORD record
ord-4a0d2e13f2e54af8857cd02a2ed3add9
Source dataset
uspto-grants-2012_06
Patent number
US08202866B2

Linked notes

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