Réaction #169648

Équation de réaction

dichloromethane

methyl 1-amino-4-bromo-2-naphthoate hydrobromide

(2-chloro-5-pyridyl)methylzinc chloride

water

water

→

methyl 1-amino-4-(4-chlorobenzyl)-2-naphthoate

Solvants

THF

Conditions de réaction

Traitement

1. 1
   Autrea beige solid was removed via filtration
2. 2
   ExtractionThe filtrate was extracted 2× with dichloromethane
3. 3
   Séchagethe combined organic fractions were dried over sodium sulfate
4. 4
   Filtrationfiltered
5. 5
   Concentrationconcentrated in vacuo
6. 6
   AutreThe residue was purified via silica gel chromatography
7. 7
   Lavageeluting with 0-20% ethyl acetate in hexanes

Mode opératoire

To a solution of methyl 1-amino-4-bromo-2-naphthoate hydrobromide (1.94 g, 5.37 mmol) in 10 mL of THF at 0° C. under an atmosphere of nitrogen was added (2-chloro-5-pyridyl)methylzinc chloride (41.6 mL, 0.5 M in THF, 83.2 mmol) and bis(tri-tert-butylphosphine)palladium(0) (0.177 g, 0.346 mmol). The reaction was warmed to rt, and after 16 h, treated with water (10 mL). The mixture was diluted dichloromethane and water, and a beige solid was removed via filtration. The filtrate was extracted 2× with dichloromethane and the combined organic fractions were dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 0-20% ethyl acetate in hexanes provide methyl 1-amino-4-(4-chlorobenzyl)-2-naphthoate that gave a proton NMR spectra consistent with theory and a mass ion (ES+) of 326.1 for [M+H]+.

Source