Potassium Carbonate → HCID 73335538, compound

Participants

Reaction Conditions

Reaction Steps

2-(4-Chloro-5-methyl-3-(trifluoromethyl)-1H-pyrazol-1-yl)-1-(6,7-dihydro-1H-pyrazolo[4,3-b]pyridin-4(5H)-yl)ethanone (104 mg, 0.3 mmol) was combined with 5-fluoro-2-bromopyridine (106 mg, 0.6 mmol), 0.3 mL of dioxane, Cu(I)I (11.4 mg, 0.06 mmol, 20%), (±)-trans-N,N′-dimethylcyclohexane-1,2-diamine (21.3 mg, 0.15 mmol, 50%), and K2CO3 (83 mg, 0.6 mmol). The slurry was heated to 120° C. until complete (approx 3 hours). The reaction mixture was diluted in 4 mL of EtOAc and washed with 2×H2O. The organic layer was concentrated and the residue was purified by reverse phase HPLC (C18 column, acetonitrile-H2O with 0.1% TFA as eluent) to provide the title compound as a white solid. 1H NMR (400 MHz, CDCl3, mixture of rotamers) δ 8.91 (s, 0.8H), 8.33 (d, J=2.7 Hz, 0.2H), 8.28 (d, J=2.9 Hz, 0.8H), 7.87-7.94 (m, 1H), 7.68-7.77 (m, 1H), 5.42 (s, 1.6H), 5.41 (s, 0.4H), 3.93 (s, 1.6H), 3.88 (s, 0.4H), 2.88 (t, J=6.4 Hz, 2H), 2.29 (s, 0.6H), 2.28 (s, 2.4H), 2.18 (m, 2H); MS: (ES) m/z calculated for C18H16ClF4N6O [M+H]+ 443.1, found 443.0.

Provenance & Evidence