Sodium Carbonate → 1-(6-chloro-2,3-dimethylquinolin-4-yl)-6-(1H-pyrazol-4-yl)-1H-indole-3-carbonitrile

Participants

Reaction Steps

A solution of 6-bromo-1-(6-chloro-2,3-dimethylquinolin-4-yl)-1H-indole-3-carbonitrile (0.2 g, 0.49 mmol), 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.188 g, 0.97 mmol), and Pd(PPh3)4 (0.056 g, 0.049 mmol) in a 2M aqueous solution of Na2CO3 (1.5 mL) and DMF (5 mL) was stirred at 100° C. overnight. After this time the reaction mixture was allowed to cool to rt and poured into ice water. The resulting precipitate was filtered and purified via flash column chromatography to give 1-(6-chloro-2,3-dimethylquinolin-4-yl)-6-(1H-pyrazol-4-yl)-1H-indole-3-carbonitrile. 1H NMR (500 MHz, chloroform-d) δ ppm 8.02 (1H, d, J=9.0 Hz), 7.82 (1H, d, J=8.3 Hz), 7.64 (2H, m), 7.58 (2H, m), 7.49 (1H, dt, J=8.3, 0.7 Hz), 6.96 (1H, d, J=2.4 Hz), 6.82 (1H, s), 2.76 (3H, s), 2.01 (3H, s). Mass Spectrum (ESI) m/e=398 (M+1).

Provenance & Evidence