Sodium Bicarbonate → methyl 6-(4-(4-cyano-2-fluorophenyl)-5-methoxy-1H-pyrazol-1-yl)nicotinate

Beteiligte Stoffe

Reaktionsschritte

Combined methyl 6-(4-bromo-5-methoxy-1H-pyrazol-1-yl)nicotinate (1.0 g, 3.20 mmol), 3-fluoro-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzonitrile (1.583 g, 6.41 mmol), dichloro[1,1′-bis(di-t-butylphosphino)ferrocene]palladium(II) (0.209 g, 0.320 mmol) and sodium bicarbonate (1.346 g, 16.02 mmol) in dioxane (10 mL) and water (2.5 mL) and heated at 110° C. for 30 min in the microwave. The reaction was diluted with EtOAc, concentrated on Celite® and purified on a 100 g NH column (Moritex) eluted with 10 to 80% EtOAc in hexanes to give the title compound (1.0 g) which was used without further purification. MS m/z 353 [M+H]+. 1H NMR (400 MHz, DMSO-d6) δ ppm 3.90 (s, 3H) 3.92 (s, 3H) 7.81 (dd, J=8.1, 1.8 Hz, 1H) 7.89-7.98 (m, 2H) 8.00 (dd, J=10.7, 1.6 Hz, 1H) 8.09 (d, J=3.0 Hz, 1H) 8.51 (dd, J=8.6, 2.3 Hz, 1H) 9.08 (dd, J=2.3, 0.5 Hz, 1H).

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