Reaktion #44249

Reaktionsgleichung

4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

2-fluoro-4-iodoaniline

LiHMDS

→

desired product

Ausbeute 39.6%

4-(2-fluoro-4-iodophenylamino)-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid

Ausbeute 39.6%

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONAfter complete addition
2. 2
   SonstigeThe reaction mixture was quenched with 6 N aqueous HCl (8 mL) at 0° C.
3. 3
   Temperaturwarmed to room temperature
4. 4
   workup.STIRRINGstirred for 1.5 hours
5. 5
   FiltrationThe precipitates were filtered
6. 6
   Waschenwashed with water and ether
7. 7
   Sonstigetriturated with ether

Vorschrift

To a suspension of 4-chloro-1,5-dimethyl-6-oxo-1,6-dihydropyridazine-3-carboxylic acid (200 mg, 0.99 mmol) and 2-fluoro-4-iodoaniline (478 mg, 1.97 mmol) in THF (6.5 mL) at −78° C. was slowly added a solution of LiHMDS (3.00 mL, 3.00 mmol, 1 M solution in THF). After complete addition, the resulting mixture was slowly warmed to room temperature and stirred for 4 hours. The reaction mixture was quenched with 6 N aqueous HCl (8 mL) at 0° C., warmed to room temperature, and stirred for 1.5 hours. The precipitates were filtered, washed with water and ether, and triturated with ether to afford 158 mg (38%) of the desired product.

Quelle