Cesium carbonate → N-methyl-2-[[2-[(2-methylpyrazol-3-yl)amino]-5-(trifluoromethyl)-4-pyridyl]amino]benzamide

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

2-[[2-chloro-5-(trifluoromethyl)pyridin-4-yl]amino]-N-methylbenzamide (100 mg, 0.30 mmol, Example 2.01), 1-methylpyrazol-5-amine (58.9 mg, 0.61 mmol), cesium carbonate (119 mg, 0.36 mmol), 9,9-dimethyl-4,5-bis(diphenylphosphino)xanthene (28.1 mg, 0.05 mmol) and palladium(II) acetate (5.45 mg, 0.02 mmol) were suspended in dioxane (1.5 mL) in a sealed tube. The reaction was degased, purged with nitrogen and heated to 100° C. for 18 hours. The reaction mixture was filtered and purified by preparative HPLC using a Waters X-Bridge reverse-phase column (C-18, 5 microns silica, 19 mm diameter, 100 mm length, flow rate of 40 ml/minute) and decreasingly polar mixtures of water (containing 0.2% ammonium carbonate) and acetonitrile as eluent. The fractions containing the desired compound were evaporated to dryness to afford the title compound (62 mg, 52.4%) as a pale orange solid. 1H NMR spectrum (500 MHz, DMSO): 2.77 (d, 3H), 3.63 (s, 3H), 6.21 (d, 1H), 6.70 (s, 1H), 7.13 (ddd, 1H), 7.32 (d, 1H), 7.49 (ddd, 1H), 7.55 (d, 1H), 7.71 (dd, 1H), 8.25 (s, 1H), 8.68 (q, 1H), 9.03 (s, 1H), 10.20 (s, 1H); Mass spectrum: ESI+ MH+ 391.

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