Reaktion #49016

Reaktionsgleichung

dichloroacetic acid

(E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[methylcarbamoylmethoxyimino-methyl]-benzamide

dichloroacetic acid

→

3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(methylcarbamoylmethoxyamino-methyl)-benzamide

Ausbeute 54.1%

Lösungsmittel

methylene chloride

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGthe mixture was stirred for 1 day
2. 2
   Waschenwashed with saturated brine (2×20 ml)
3. 3
   TrocknenThe organic layer was dried over anhydrous magnesium sulfate
4. 4
   Einengenconcentrated under reduced pressure
5. 5
   SonstigeThe resultant residue was purified by preparative TLC (EtOAc/MeOH (9:1))

Vorschrift

To a solution of (E)-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[methylcarbamoylmethoxyimino-methyl]-benzamide (69.8 mg, 0.12 mmol) obtained in Step C in methylene chloride (15 ml) were added borane-pyridine complex (199 μl, 1.92 mmol) and dichloroacetic acid (162 μl, 1.92 mmol) at room temperature, and the mixture was stirred for 3.5 days. Additional borane-pyridine complex (199 μl, 1.92 mmol) and dichloroacetic acid (162 μl, 1.92 mmol) were added, and the mixture was stirred for 1 day. The reaction mixture was diluted with methylene chloride (20 ml), and washed with saturated brine (2×20 ml). The organic layer was dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The resultant residue was purified by preparative TLC (EtOAc/MeOH (9:1)) to give 3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-(methylcarbamoylmethoxyamino-methyl)-benzamide (36.9 mg, 53%) as a colorless oil.

Quelle