Реакция #1334361

Уравнение реакции

HCl

benzoxazinone

THF

2-amino-5-chloropyridine

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

→

title compound

Выход 39.0%

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

Выход 39.0%

Условия реакции

Обработка

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

Методика

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.

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