反応 #44256

反応方程式

methyl 2-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate

(S)—O-(2-(tert-butyldimethylsilyloxy)propyl)hydroxylamine

lithium bis(trimethylsilyl)amide

→

(S)-2-(4-Bromo-2-fluorophenylamino)-N-(2-(tert-butyldimethylsilyloxy)propoxy)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxamide

溶媒

THF

反応条件

後処理

1. 1
   その他at 0° C.
2. 2
   workup.ADDITIONAfter addition
3. 3
   その他quenched by with saturated NaHCO3
4. 4
   その他The reaction mixture was partitioned between EtOAc
5. 5
   その他The layers were separated
6. 6
   抽出the aqueous layer was back-extracted with EtOAc (1×)
7. 7
   乾燥The combined organic layers were dried (Na2SO4)
8. 8
   ろ過filtered
9. 9
   濃縮concentrated under reduced pressure
10. 10
    その他to yield a crude brown solid that
11. 11
    その他was used without further purification in the next step

実験手順

To a solution of methyl 2-(4-bromo-2-fluorophenylamino)-1-methyl-6-oxo-1,6-dihydropyridine-3-carboxylate (0.050 g, 0.14 mmol) and (S)—O-(2-(tert-butyldimethylsilyloxy)propyl)hydroxylamine (0.072 g, 0.35 mmol) in THF (1.50 mL) at 0° C. was slowly added lithium bis(trimethylsilyl)amide (0.70 ml, 0.70 mmol). After addition, the reaction mixture was stirred for 1 hour at room temperature and then quenched by with saturated NaHCO3. The reaction mixture was partitioned between EtOAc and sat NaCl. The layers were separated and the aqueous layer was back-extracted with EtOAc (1×). The combined organic layers were dried (Na2SO4), filtered and concentrated under reduced pressure to yield a crude brown solid that was used without further purification in the next step.

出典