Cesium carbonate → HCID 59843028, compound

Participants

Reaction Conditions

Reaction Steps

To a 5 mL CEM microwave tube was added 2-(2-fluoro-5-(4-methylthiophen-2-yl)pyridin-3-yl)ethanol (0.06 g, 0.3 mmol), 4-chloro-7-methoxyquinoline (0.10 g, 0.5 mmol), racemic-2-(di-t-butylphosphino)-1,1′-binaphthyl (0.04 g, 0.1 mmol), palladium (II) acetate (0.02 g, 0.1 mmol), cesium carbonate (0.2 g, 0.5 mmol), and toluene (4 mL). The vial was sealed and heated at 80° C. in the closed system for 3 h. The reaction mixture was passed through the celite to separate the inorganic salt. Solvent was removed. The crude product was purified using SiO2 chromatography with CH2Cl2:MeOH (98%:2%) to afford the product as brown solid. MS (ESI pos. ion) m/z (MH+): 395.3. Calc'd exact mass for C22H19FN2O2S: 394.1. 1H NMR (300 MHz, Chloroform-d) δ ppm 2.30 (s, 3 H) 3.31 (t, J=6.21 Hz, 2 H) 3.94 (s, 3 H) 4.46 (t, J=6.21 Hz, 2 H) 6.65 (d, J=5.41 Hz, 1 H) 6.94 (s, 1 H) 7.07 (s, 1 H) 7.12 (dd, J=9.13, 2.56 Hz, 1 H) 7.36 (d, J=2.48 Hz, 1 H) 7.95 (dd, J=8.99, 2.41 Hz, 1 H) 8.05 (d, J=9.06 Hz, 1 H) 8.33 (s, 1 H) 8.67 (d, J=5.26 Hz, 1 H).

Provenance & Evidence