Cesium carbonate → HCID 57635862, compound

Participants

Reaction Conditions

Reaction Steps

To a dried 100 mL flask was added 3-tert-butyl-1-(2,5-dimethylphenyl)-1H-pyrazol-5-amine (1.68 g, 6.9 mmol), synthesized in the same manner as Intermediate F using Intermediate A, ethyl 3-{[(trifluoromethyl)sulfonyl]oxy}pyridine-2-carboxylate (1.88 g, 6.28 mmol) (from step 1), Pd2(dba)3 (0.28 g, 0.31 mmol), BINAP (0.39 g, 0.63 mmol), and Cs2CO3 (4.1 g, 12.5 mmol). The flask was degassed followed by addition of toluene (10 mL) and the mixture was then heated to 110° C. for 4 h. The mixture was cooled to rt, filtered through a Celite® plug with ethyl acetate as eluent, concentrated to dryness, and purified by silica gel flash chromatography with 10 to 30% of ethyl acetate in hexanes to afford 1.4 g (57%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 9.29 (s, 1H), 8.19 (dd, 1H), 7.82 (dd, 1H), 7.41 (dd, 1H), 7.31 (dd, 1H), 7.19 (d, 2H), 6.18 (s, 1H), 4.28 (q, 2H), 2.01 (s, 6H), 1.39 (s, 9H), 1.32 (t, 3H); ES-MS m/z 393.2 (MH+); HPLC RT (min) 3.57.

Provenance & Evidence