Réaction #2028944

Équation de réaction

sodium bicarbonate

methane sulfonamide

H2O

4-trifluoromethyl phenylboronic acid

DMF

→

methyl 4-[(methylsulfonyl)amino]-4′-(trifluoromethyl)biphenyl-3-carboxylate

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled
2. 2
   Filtrationfiltered through celite
3. 3
   Lavagewashed with EtoAc (50 mL)
4. 4
   LavageThe combined organics were washed with water, brine
5. 5
   Séchagedried over Na2SO4
6. 6
   Concentrationconcentrated
7. 7
   AutreThe product (180 mg, 49%) was purified by preparative TLC
8. 8
   Lavageby eluting with CH2Cl2

Mode opératoire

To a solution of methane sulfonamide (308 mg, 1 mmol) in DMF:H2O (10 mL; 9:1), 4-trifluoromethyl phenylboronic acid (227 mg, 1.2 mmol) was added followed by sodium bicarbonate (252 mg, 3 mmol) and stirred under nitrogen for 5 min. To the reaction mixture Pd(PPh3)4 (55 mg, 0.05 mmol) was added and heated at 90° C. for 90 min. The reaction mixture was cooled, filtered through celite, washed with EtoAc (50 mL). The combined organics were washed with water, brine, dried over Na2SO4 and concentrated. The product (180 mg, 49%) was purified by preparative TLC by eluting with CH2Cl2.to give methyl 4-[(methylsulfonyl)amino]-4′-(trifluoromethyl)biphenyl-3-carboxylate, PT-121.

Source