Reaktion #424777

Reaktionsgleichung

cesium carbonate

rac-BINAP

methyl 3-bromo-1-naphthalenecarboxylate

2-methoxyethylamine

→

title compound

Methyl 3-{[2-(methyloxy)ethyl]amino}-1-naphthalenecarboxylate

Lösungsmittel

ether

toluene

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe vessel was repeatedly evacuated
2. 2
   workup.ADDITIONback-filled with nitrogen
3. 3
   TemperaturThe now black suspension was cooled to RT
4. 4
   Filtrationfiltered through a pad of celite
5. 5
   SonstigeConcentration of the filtrate in vacuo afforded a brown oil that
6. 6
   Sonstigecan be purified further by way of column chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc)

Vorschrift

Freshly purified cesium carbonate (1.4 eq.), palladium(II) acetate (0.02 eq.) and rac-BINAP (0.03 eq.) were combined in anhydrous toluene (0.25 M). The vessel was repeatedly evacuated and back-filled with nitrogen. Finally, methyl 3-bromo-1-naphthalenecarboxylate (1 eq.) and 2-methoxyethylamine (1.2 eq.) were added and the resulting mixture was heated at 100° C. for 20 h. The now black suspension was cooled to RT, diluted with ether and filtered through a pad of celite. Concentration of the filtrate in vacuo afforded a brown oil that can be purified further by way of column chromatography (SiO2, 19:1 (v/v) Hex:EtOAc→1:1 (v/v) Hex:EtOAc) to afford the title compound as a yellow oil.

Quelle