Sodium Carbonate → Imidazo[5,1-f][1,2,4]triazin-4-amine, N,7-dimethyl-5-[1-methyl-5-[4-(trifluoromethyl)phenyl]-1H-pyrazol-4-yl]-

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Reaction Steps

5-(5-Bromo-1-methyl-1H-pyrazol-4-yl)-N,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-amine (500 mg, 1.55 mmol), [4-(trifluoromethyl)phenyl]boronic acid (590 mg, 3.11 mmol), sodium carbonate (329 mg, 3.10 mmol), tetrakis(triphenylphosphine)palladium(0) (179 mg, 0.155 mmol) and ethanol (10 mL) were combined in a microwave vessel. The reaction was subjected to microwave irradiation at 130° C. for 45 minutes at 200 W. The reaction was dried over sodium sulfate, filtered and concentrated in vacuo. Purification via silica gel chromatography (Eluant: 20% tetrahydrofuran in dichloromethane) provided the product as a light yellow solid. Yield: 423 mg, 1.13 mmol, 73%. LCMS m/z 388.2 (M+1). 1H NMR (400 MHz, CDCl3) δ 2.62 (s, 3H), 2.99 (d, J=4.9 Hz, 3H), 3.96 (s, 3H), 5.46-5.53 (m, 1H), 7.60 (br AB quartet, JAB=8 Hz, ΔvAB=48 Hz, 4H), 7.73 (s, 1H), 7.90 (s, 1H).

Provenance & Evidence