Reaktion #1075913

Reaktionsgleichung

benzoxazinone

THF

2-amino-5-chloropyridine

2-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide

→

title compound

Ausbeute 39.0%

2-(4-tert-Butylbenzoylamino)-N-(5-chloropyridin-2-yl)-5-methoxycarbonylbenzamide

Ausbeute 39.0%

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe solution was cooled in an ice bath
2. 2
   workup.WAITwas continued for 15 min
3. 3
   Sonstigethe reaction mixture was quenched with 100 mL cold dilute HCl
4. 4
   ExtraktionThe mixture was extracted with 100 mL EtOAc
5. 5
   Waschenthe organic layer was washed with 100 mL cold dilute HCl
6. 6
   Trocknendried (MgSO4)
7. 7
   Einengenconcentrated under vacuum
8. 8
   SonstigeThe crude product was chromatographed over silica (0 to 30% EtOAc in hexane gradient)

Vorschrift

Into 25 mL THF was dissolved 0.174 g (0.5 mmol) of the above benzoxazinone intermediate. The solution was cooled in an ice bath and placed under nitrogen atmosphere. To the mixture was added 1.5 mL (0.6 mmol) of a 0.4 M solution of the magnesium salt of 2-amino-5-chloropyridine (See Prep. D, Example 278). After 30 min, an additional 1.5 mL (0.6 mmol) of the magnesium salt was added. Stirring was continued for 15 min, and the reaction mixture was quenched with 100 mL cold dilute HCl. The mixture was extracted with 100 mL EtOAc, and the organic layer was washed with 100 mL cold dilute HCl, dried (MgSO4), and concentrated under vacuum. The crude product was chromatographed over silica (0 to 30% EtOAc in hexane gradient), giving 91 mg (39%) of title compound as a crystalline solid.

Quelle