Reaktion #2028944

Reaktionsgleichung

sodium bicarbonate

methane sulfonamide

H2O

4-trifluoromethyl phenylboronic acid

DMF

→

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

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled
2. 2
   Filtrationfiltered through celite
3. 3
   Waschenwashed with EtoAc (50 mL)
4. 4
   WaschenThe combined organics were washed with water, brine
5. 5
   Trocknendried over Na2SO4
6. 6
   Einengenconcentrated
7. 7
   SonstigeThe product (180 mg, 49%) was purified by preparative TLC
8. 8
   Waschenby eluting with CH2Cl2

Vorschrift

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.

Quelle