Cesium carbonate → HCID 90152010, compound

Participants

Reaction Conditions

Reaction Steps

Pd2(dba)3 (0.068 g, 0.074 mmol) and BINAP (0.046 g, 0.074 mmol) were added to a solution of 3G (0.5 g, 1.478 mmol) in 10 mL of toluene under argon atmosphere, followed by cesium carbonate (1.44 g, 4.43 mmol) and 5-bromo-2-(trifluoromethyl)pyridine (0.334 g, 1.478 mmol). The mixture was degassed for 10 min. The reaction mixture was stirred at 100° C. for 6 h and allowed to warm to room temperature. The reaction mixture was diluted with ethyl acetate and water. The separated organic layer was dried over sodium sulfate and filtered, and the filtrate was concentrated. The crude product was purified by flash chromatography using 8% ethyl acetate in hexane to afford the title compound 3H (0.4 g, 53%) as a solid. 1H NMR (300 MHz, DMSO-d6): δ 9.34 (s, 1H), 8.60 (d, J=2.7 Hz, 1H), 8.51 (d, J=2.2 Hz, 1H), 8.08-7.91 (m, 4H), 7.88-7.63 (m, 3H), 4.01 (q, J=7.1 Hz, 2H), 3.08 (m, 2H), 2.85 (d, J=15.9 Hz, 1H), 2.50-2.29 (m, 2H), 1.93 (m, 1H), 1.19 (s, 3H), 1.13 (t, J=6.9 Hz, 3H). ESI-MS m/z: 484 (M+H)+.

Provenance & Evidence