Réaction #1125835

Équation de réaction

4-bromopicolinic acid

triethylamine

carbonyl diimidazole

→

4-bromo-pyridine-2-carboxylic acid methoxy-methyl-amide

Rendement 86.0%

4-Bromo-pyridine-2-carboxylic acid methoxy-methyl-amide

Rendement 86.0%

Solvants

THF

Conditions de réaction

Traitement

1. 1
   AutreUpon completion of the reaction
2. 2
   Autrethe reaction mixture is quenched with 100 mL of water
3. 3
   Extractionextracted with 2×150 mL of ethyl acetate
4. 4
   ConcentrationThe combined organic layers are concentrated
5. 5
   Autrepurified by chromatography (hexanes 95%, EtOAc 5% step gradient)

Mode opératoire

To a solution of commercially-available 4-bromopicolinic acid (10.0 g, 49.5 mmole) in 200 mL of anhydrous THF at room temperature is added N,O-hydroxylamine hydrochloride (4.83 g, 49.5 mmol), triethylamine (6.9 mL, 49.5 mmol), carbonyl diimidazole (CDl) (12.0 g, 74.3 mmol) and N,N-dimethyl amino pyridine (DMAP) (20 mg, 0.16 mmol). After stirring at room temperature for 4 hours, an aliquot is taken and injected on LC-MS to check the reaction progress. Upon completion of the reaction, the reaction mixture is quenched with 100 mL of water and extracted with 2×150 mL of ethyl acetate. The combined organic layers are concentrated and purified by chromatography (hexanes 95%, EtOAc 5% step gradient) to give 4-bromo-pyridine-2-carboxylic acid methoxy-methyl-amide (1) as a thick yellow oil (10.4 g, yield 86%) MS ES+247.02.

Source