Reaktion #677206

Reaktionsgleichung

HCl

2-Chloro-4-methylpyrimidine

LiHMDS

methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate

→

title compound

Ausbeute 71.0%

N-{3-[(2-Chloro-4-pyrimidinyl)acetyl]-2-fluorophenyl}-2,6-difluorobenzenesulfonamide

Ausbeute 71.0%

Lösungsmittel

THF

THF

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeIn a 1000 mL flask was placed
2. 2
   SonstigeThe flask was placed in an ice/water bath
3. 3
   workup.ADDITIONAfter the addition
4. 4
   Sonstigethe layers were separated
5. 5
   ExtraktionThe aqueous layer was extracted twice with EtOAc
6. 6
   Waschenthe combined organic layer was washed once with brine
7. 7
   Trocknendried over NaSO4
8. 8
   Einengenconcentrated
9. 9
   SonstigeThe residue was triturated with EtOAc/ether

Vorschrift

In a 1000 mL flask was placed methyl 3-{[(2,6-difluorophenyl)sulfonyl]amino}-2-fluorobenzoate (9.64 g, 27.9 mmol) and THF (200 mL) was added. The flask was placed in an ice/water bath and LiHMDS (90 mL, 90 mmol) was added. 2-Chloro-4-methylpyrimidine (4.5 g, 35.0 mmol) in THF (60 mL) was added dropwise via addition funnel. After the addition was complete, the reaction was allowed to warm to 20° C. over 1 h. The THF volume was reduced to half under reduced pressure and then treated with 6N HCl. EtOAc was added and the layers were separated. The aqueous layer was extracted twice with EtOAc and the combined organic layer was washed once with brine, dried over NaSO4, and concentrated. The residue was triturated with EtOAc/ether to afford 8.71 g (71%) of the title compound of Step D. MS (ESI): 442 [M+H]+.

Quelle