Reacción #2175505

Ecuación de reacción

(S)-4-iodo-N-(quinuclidin-3-yl)benzamide

cesium carbonate

4-(trifluoromethyl)phenylboronic acid

→

(S)—N-(quinuclidin-3-yl)-4′-(trifluoromethyl)biphenyl-4-carboxamide

Rendimiento 65.4%

Disolventes

Acetonitrile

water

Condiciones de reacción

Tratamiento posterior

1. 1
   OtroThe mixture was degassed by sonication for 20 minutes
2. 2
   FiltraciónThe reaction mixture was filtered through pad of celite
3. 3
   Lavadowashed with acetone, solution
4. 4
   Concentraciónwas concentrated under vacuum to oil

Procedimiento

4-(trifluoromethyl)phenylboronic acid (20.9 mg, 0.11 mmol) was added to a flask charged with (S)-4-iodo-N-(quinuclidin-3-yl)benzamide (35.6 mg, 0.1 mmol), cesium carbonate (81.5 mg, 0.25 mmol) in 2 ml of Acetonitrile and 2 ml of water. The mixture was degassed by sonication for 20 minutes followed by charging catalytic amount of Palladium (II) acetate and place under nitrogen to stirred for 3 hours. The reaction mixture was filtered through pad of celite and washed with acetone, solution was concentrated under vacuum to oil. Preparative HPLC instrument was used to obtain pure (S)—N-(quinuclidin-3-yl)-4′-(trifluoromethyl)biphenyl-4-carboxamide (24.5 mg, 65% yield). 1H NMR (400 MHz, CDCl3) δ (ppm): 7.80 (d, J=8 Hz, 2H), 7.63 (m, 4H), 7.58 (d, J=8 Hz, 2H), 6.33 (d, 1H), 4.11 (m, 1H), 3.38 (m, 1H), 2.80 (m, 4H), 2.56 (ddd, J=6, 14, 6 Hz, 1H), 2.00 (m, 1H), 1.65 (m, 3H), 1.47 (m, 1H). C21H21F3N2O=374.16 LCMS (M+H): m/z 375

Fuente