3-Nitrophenylboronic Acid → HCID 57502368, compound

Participants

Reaction Steps

5-(3-Aminophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine. 543-Nitrophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine was prepared from 5-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-amine, 3-nitro-phenylboronic acid and phenyl bromide according to the procedure described for the synthesis of 5-(furan-3-yl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine. A mixture of 5-(3-nitrophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (170 mg, 0.51 mmol), zinc dust (338 mg, 5.1 mmol), and ammonium chloride (270 mg, 5.1 mmol) in a mixture of methanol and tetrahydrofuran (v/v, 1:1, 8 mL) at room temperature overnight. The reaction mixture was filtered through celite, and the filtrate was concentrated in vacuo to give the crude product, which was washed with ethyl ether to give 5-(3-aminophenyl)-N-phenyl-[1,2,4]triazolo[1,5-a]pyridin-2-amine (79 mg, 51% yield). 1H NMR (400 MHz, METHANOL-d4) δ (ppm) 7.62-7.59 (m, 3H), 7.44 (m, 1H), 7.37 (m, 1H), 7.30-7.24 (m, 4H), 7.08 (m, 1H), 6.89 (m, 2H); MS (ESI): m/z 302.1 [M+1]+.

Provenance & Evidence