Cesium carbonate → HCID 57635865, compound

Participants

Reaction Conditions

Reaction Steps

To a dried 15 mL tube was added 1-(2-chlorophenyl)-3-(4-fluorophenyl)-1H-pyrazol-5-amine (300 mg, 1.04 mmol), synthesized in the same manner as intermediate G, ethyl 2-chloronicotinate (194 mg, 1.04 mmol), Pd2(dba)3 (48 mg, 0.05 mmol), BINAP (65 mg, 0.10 mmol), and Cs2CO3 (679 mg, 2.09 mmol). The flask was degassed followed by addition of toluene (4 mL) and the mixture was then heated to 110° C. for 20 h. The mixture was cooled to rt, filtered through a silica gel plug using ethyl acetate as eluent, concentrated to dryness, and subjected to HPLC purification using a gradient elution from 45% to 90% acetonitrile in water to afford 410 mg (90%) of the desired product. 1H NMR (300 MHz, CD2Cl2) δ 10.17 (s, 1H), 8.46 (dd, 1H), 8.22 (dd, 1H), 7.89 (dd, 2H), 7.48-7.64 (m, 4H), 7.23 (s, 1H), 7.12 (t, 2H), 7.84 (dd, 1H), 4.24 (q, 2H), 1.32 (t, 3H); ES-MS m/z 437.2 (MH+); HPLC RT (min) 4.38.

Provenance & Evidence