Acetic Acid → 5-(4-Methoxyphenyl)-N-(4-(4-methylpiperazin-1-yl)phenyl)-[1,2,4]triazolo[1,5-a]pyridin-2-amine

Participants

Reaction Conditions

Reaction Steps

A solution of 4-(4-aminophenyl)-1-methylpiperazine (163 mg, 0.86 mmol), 2-dicyclohexylphosphino-2′,4′,6′-triisopropylbiphenyl (54 mg, 0.11 mmol), sodium tert-butoxide (103 mg, 1 mmol), and 2-iodo-5-(4-methoxyphenyl)-[1,2,4]triazolo[1,5-a]pyridine (150 mg, 0.43 mmol) in dimethylformamide (4 mL) was degassed by evacuation of the reaction vessel followed by N2 purge (3×). To this mixture was added trisdibenzylideneacetone-bispalladium (52 mg, 0.06 mmol), and the reaction mixture was further degassed. The reaction mixture was heated to 100° C. After 2 h, acetic acid (60 mg, 1 mmol) was added, the resulting mixture was filtered and concentrated. Purification by reverse phase HPLC provided product (60 mg, 30%). 1H NMR (400 MHz, CD3OD), δ: 8.10 (d, 2H), 7.7 (m, 1H), 7.6 (d, 2H), 7.35 (t, 1H), 7.20 (m, 3H), 7.0 (d, 2H), 3.9 (s, 3H), 3.2 (t, 4H), 2.7 (t, 4H), 2.4 (s, 3H); ES-MS m/z 415.3.

Provenance & Evidence