反応 #1017531

反応方程式

NaHCO3

N-((4S,6S)-4-(6-bromo-3-fluoropyridin-2-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide

1,8-diazabicyclo-[5.4.0]undec-7-ene

→

(4S,6S)-4-(6-bromo-3-fluoropyridin-2-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine

溶媒

MeOH

反応条件

後処理

1. 1
   その他The vial was sealed
2. 2
   workup.ADDITIONThe reaction mixture was poured
3. 3
   抽出extracted with EtOAc
4. 4
   洗浄The combined extracts were washed with water
5. 5
   乾燥dried (Na2SO4)
6. 6
   濃縮concentrated onto silica
7. 7
   その他Purification by silica gel chromatography (Gradient: 0.0 to 9.0% MeOH/CH2Cl2)

実験手順

To a 20 mL resealable vial was added N-((4S,6S)-4-(6-bromo-3-fluoropyridin-2-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-yl)benzamide (0.500 g, 1.046 mmol), MeOH (10 mL) and finally 1,8-diazabicyclo-[5.4.0]undec-7-ene (Aldrich; 0.312 mL, 2.091 mmol). The vial was sealed and stirred at 75° C. for 2 h. The reaction mixture was poured into sat NaHCO3 and extracted with EtOAc. The combined extracts were washed with water and then dried (Na2SO4) and concentrated onto silica. Purification by silica gel chromatography (Gradient: 0.0 to 9.0% MeOH/CH2Cl2) afforded (4S,6S)-4-(6-bromo-3-fluoropyridin-2-yl)-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-2-amine. The material still contained some impurities. MS m/z=375.8 [M+H]+. Calculated for C11H9BrF5N3O: 375.0.

出典