반응 #1334361

반응 방정식

HCl

benzoxazinone

THF

2-amino-5-chloropyridine

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

→

title compound

수율 39.0%

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

수율 39.0%

반응 조건

후처리

1. 1
   온도The solution was cooled in an ice bath
2. 2
   workup.WAITwas continued for 15 min
3. 3
   추출The mixture was extracted with 100 mL EtOAc
4. 4
   세척the organic layer was washed with 100 mL cold dilute HCl
5. 5
   건조dried (MgSO4)
6. 6
   농축concentrated under vacuum
7. 7
   기타The crude product was chromatographed over silica (0 to 30% EtOAc in hexane gradient)

실험 절차

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 quinched 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.

출처