Sodium Carbonate → HCID 86669723, compound

Participants

Reaction Steps

5-Bromo-1-methyl-1H-pyrazol-4-yl)-N,7-dimethylimidazo[5,1-f][1,2,4]triazin-4-amine (1.18 g, 3.66 mmol), (4-formylphenyl)boronic acid (604 mg, 4.03 mmol), tetrakis(triphenylphosphine)palladium(0) (423 mg, 0.366 mmol) and sodium carbonate (776 mg, 7.32 mmol) were combined in ethanol (20 mL), and the reaction mixture was heated at reflux for 18 hours. After cooling, solvent was removed in vacuo, and the residue was partitioned between ethyl acetate and water. The organic layer was dried over sodium sulfate, filtered, and concentrated under reduced pressure. Purification via silica gel chromatography (Gradient: 0% to 100% [18:1:1 ethyl acetate/methanol/triethylamine] in heptane) provided the crude product (900 mg), which was taken directly to the next step. LCMS m/z 348.2 (M+1). 1H NMR (400 MHz, CD3OD), product peaks only: δ 2.57 (s, 3H), 2.82 (s, 3H), 3.95 (s, 3H), 7.51 (br d, J=8.2 Hz, 2H), 7.75 (s, 1H), 7.78 (s, 1H), 7.92 (br d, J=8.5 Hz, 2H), 9.98 (s, 1H).

Provenance & Evidence