反応 #67796

反応方程式

lithium bis(trimethylsilyl)amide

3-fluoroisonicotinic acid

2-chloro-4-iodoaniline

lithium bis(trimethylsilyl)amide

→

3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid

溶媒

tetrahydrofuran

THF

反応条件

後処理

1. 1
   workup.STIRRINGThe resulting green colored solution was stirred for 15 min
2. 2
   workup.ADDITIONTo this green colored solution the lithiated acid solution was added
3. 3
   その他The cold bath was removed
4. 4
   workup.STIRRINGstirred overnight
5. 5
   ろ過The mixture was filtered
6. 6
   workup.ADDITIONthe crude was diluted with EtOAc (400 ml)
7. 7
   洗浄It was then washed with dilute HCl (25 ml), H2O (25 ml)
8. 8
   その他dried
9. 9
   その他During concentration of the solvent, 3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid was separated out as an yellow solid

実験手順

To suspension of 3-fluoroisonicotinic acid (2.00 g, 14.17 mmol, in tetrahydrofuran (50 ml) at −78° C. was added lithium bis(trimethylsilyl)amide (14.3 ml, 17.01 mmol). The dark colored suspension was stirred for 15 min. In another flask, to a solution of 2-chloro-4-iodoaniline (4.7 g, 18.43 mmol) in THF (50 ml) was added lithium bis(trimethylsilyl)amide (24.9 ml, 29.77 mmol) at −78° C. under N2. The resulting green colored solution was stirred for 15 min. To this green colored solution the lithiated acid solution was added. The cold bath was removed, allowed to warm to room temperature, and stirred overnight. The mixture was filtered, and the crude was diluted with EtOAc (400 ml). It was then washed with dilute HCl (25 ml), H2O (25 ml), and dried. During concentration of the solvent, 3-[(2-chloro-4-iodophenyl)amino]isonicotinic acid was separated out as an yellow solid. (1.3 g, 24%)

出典