Reaktion #1451707

Reaktionsgleichung

bromide

N-(4-Amino-6-bromo-5-cyano-pyridin-2-yl)-acetamide

Na2CO3

Phenyl boric acid

→

titled compound

Ausbeute 72.7%

N-(4-amino-5-cyano-6-phenylpyridin-2-yl)acetamide

Ausbeute 72.7%

Lösungsmittel

DMF THF H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe resulting mixture was capped
2. 2
   SonstigeThe crude mixture was partitioned between EtOAc and water
3. 3
   WaschenThe organic layer washed with water and brine
4. 4
   Trocknendried over Na2SO4
5. 5
   Sonstigeevaporated under reduced pressure
6. 6
   SonstigeThe crude residue was purified by a Gilson reverse phase HPLC

Vorschrift

A mixture of bromide from Example 65A (45 mg, 0.18 mmol), Na2CO3 (38 mg, 0.35 mmol), and Pd(PPh3)4 (10 mg, 0.009 mmol) was stirred in DMF/THF/H2O (1:1:0.5) under nitrogen in a microwave reactor vial. Phenyl boric acid (26 mg, 0.21 mmol) was added. The resulting mixture was capped and heated at 130° C. for 20 min in a microwave reactor. The crude mixture was partitioned between EtOAc and water. The organic layer washed with water and brine, dried over Na2SO4, and evaporated under reduced pressure. The crude residue was purified by a Gilson reverse phase HPLC to provide the titled compound (33 mg, 72% yield). 1H NMR (300 MHz, d6-DMSO) δ 10.44 (s, 1H), 7.74-7.68 (m, 2H), 7.55 (s, 1H), 7.52-7.46 (m, 3H), 6.98 (s, 2H), 2.08 (s, 3H). MS (ESI) m/e 253 (M+H)+; m/e 251 (M−H)−.

Quelle