反応 #1075913

反応方程式

benzoxazinone

THF

2-amino-5-chloropyridine

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

→

title compound

収率 39.0%

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

収率 39.0%

反応条件

後処理

1. 1
   温度The solution was cooled in an ice bath
2. 2
   workup.WAITwas continued for 15 min
3. 3
   その他the reaction mixture was quenched with 100 mL cold dilute HCl
4. 4
   抽出The mixture was extracted with 100 mL EtOAc
5. 5
   洗浄the organic layer was washed with 100 mL cold dilute HCl
6. 6
   乾燥dried (MgSO4)
7. 7
   濃縮concentrated under vacuum
8. 8
   その他The crude product was chromatographed over silica (0 to 30% EtOAc in hexane gradient)

実験手順

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.

出典