Réaction #682979

Équation de réaction

4-borono-2-fluorobenzoic acid

2,2-difluoro-1-phenylethanamine

DIEA

HOAt

EDC

citric acid

→

4-(2,2-difluoro-1-phenylethylcarbamoyl)-3-fluorophenylboronic acid

Solvants

THF

DMF

Conditions de réaction

Traitement

1. 1
   Extractionextracted with 2-methyl THF and EtOAc (1:1)
2. 2
   SéchageThe organic layers were dried over anhydrous Na2SO4
3. 3
   Filtrationfiltered
4. 4
   Concentrationconcentrated

Mode opératoire

To a solution of 4-borono-2-fluorobenzoic acid (200 mg, 1.087 mmol), 2,2-difluoro-1-phenylethanamine (232 mg, 1.196 mmol), and DIEA (0.570 mL, 3.26 mmol) in THF (3.866 mL) and DMF (0.483 mL) was added HOAt (296 mg, 2.175 mmol) and EDC (521 mg, 2.72 mmol). After 3 h stirring at room temperature, 10% citric acid solution was added (pH ˜3) and extracted with 2-methyl THF and EtOAc (1:1). The organic layers were dried over anhydrous Na2SO4, filtered, and concentrated. The crude 4-(2,2-difluoro-1-phenylethylcarbamoyl)-3-fluorophenylboronic acid was obtained (90%) and used for the next step without purification. LCMS (m/z): 375.3 (MH+), 0.48 min.

Source