Cesium carbonate → 4-(3-Methyl-6-quinoxalinyl)benzonitrile

Participants

Reaction Conditions

Reaction Steps

4-Cyanophenylboronic acid (588 mg, 4.0 mmol), cesium carbonate (2.2 g, 7.0 mmol), and cesium fluoride (608 mg, 4.0 mmol) were combined in H2O (15 mL) and treated with the products from Example 61B (446 mg, 2.0 mmol) in toluene (10 mL) and heated at 80° C. for 3 hours. The reaction mixture was allowed to cool to room temperature and filtered through a pad of celite. The filtrate was partitioned between IPAc (60 mL) and H2O (50 mL). The organic layer was separated, washed with 20% brine, dried with Na2SO4, filtered, and the filtrate was concentrated under vacuum to provide the title compounds which were used in the next step without further purification. MS 246 (M+H)+; 1H NMR (400 MHz, CDCl3) δ 8.71 (s, 1H), 8.69 (s, 1H), 8.02–8.20 (m, 4H), 7.84–7.90 (m, 2H), 7.70–7.76 (m, 8H), 2.73 (s, 6H); 13C NMR (400 MHz, CDCl3) δ 154.34, 154.10, 146.47, 147.17, 143.80, 142.93, 141.74, 140.62, 140.39, 140.18, 139.16, 132.49, 130.16, 129.74, 129.25, 128.71, 128.63, 128.06, 127.77, 127.74, 127.66, 127.59, 127.22, 126.73, 118.39, 118.37, 111.61, 111.51, 22.96.

Provenance & Evidence