Réaction #682974

Équation de réaction

2,2,2-trifluoro-1-phenylethanamine

4-borono-2-fluorobenzoic acid

N,N,3-trimethylbut-2-en-2-amine

EtOAc

→

crude product

(+/−)-(3-fluoro-4-((2,2,2-trifluoro-1-phenylethyl)carbamoyl)phenyl)boronic acid

Solvants

DCM

DCM

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGThe reaction was stirred at room temperature for 2 h
3. 3
   Lavagewashed with sat. sodium bicarbonate, water
4. 4
   Séchagedried over Na2SO4
5. 5
   FiltrationFiltered
6. 6
   Concentrationconcentrated

Mode opératoire

A mixture of 4-borono-2-fluorobenzoic acid (54 mg, 0.294 mmol) in DCM (1468 μL) was cooled to 0° C. Then ghosez reagent N,N,3-trimethylbut-2-en-2-amine (65.8 μL, 0.587 mmol) was added and the whole mixture was stirred at rt for 20 min. The mixture was added into a mixture of TEA (246 μL, 1.762 mmol), 2,2,2-trifluoro-1-phenylethanamine (59.1 mg, 0.338 mmol) and DCM (1468 μL). The reaction was stirred at room temperature for 2 h. To the reaction mixture was added EtOAc, and washed with sat. sodium bicarbonate, water, and dried over Na2SO4. Filtered and concentrated to provide the crude product which was taken to the next step without further purification. LCMS (m/z): 342.2 (MH+), 0.84 min.

Source