Réaction #682977

Équation de réaction

4-borono-2-fluorobenzoic acid

(R)-1-(2-fluorophenylsulfonyl)piperidin-3-amine

DIEA

HOAt

EDC

→

(R)-3-fluoro-4-(1-(2-fluorophenylsulfonyl)piperidin-3-ylcarbamoyl)phenylboronic acid

Solvants

THF

DMF

Conditions de réaction

Traitement

1. 1
   Extractionthe reaction mixture was extracted with EtOAc
2. 2
   LavageThe organic layer was washed with NaHCO3, water and brine
3. 3
   Séchagedried over anhydrous sodium sulfate
4. 4
   Filtrationfiltered off
5. 5
   Concentrationconcentrated in vacuo

Mode opératoire

To a solution of 4-borono-2-fluorobenzoic acid (160 mg, 0.870 mmol), (R)-1-(2-fluorophenylsulfonyl)piperidin-3-amine (225 mg, 0.870 mmol), and DIEA (456 μL, 2.61 mmol) in THF (1450 μL) and DMF (1450 μL) was added HOAt (237 mg, 1.740 mmol) and EDC (417 mg, 2.175 mmol). After 3 h stirring at room temperature, the reaction mixture was extracted with EtOAc. The organic layer was washed with NaHCO3, water and brine, dried over anhydrous sodium sulfate, filtered off, and concentrated in vacuo yielding (R)-3-fluoro-4-(1-(2-fluorophenylsulfonyl)piperidin-3-ylcarbamoyl)phenylboronic acid, which was used in next step reaction without purification. LCMS (m/z): 425.2 (MH+), 0.72 min.

Source