1-(propan-2-yl)-1H-pyrazol-5-amine → Ethyl 1-(1-methylethyl)-6-propyl-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

Participants

Reaction Conditions

Reaction Steps

To a solution of ethyl 2,4-dioxoheptanoate (446 mg, 2.397 mmol) in benzene (5 mL) was added 1-(1-methylethyl)-1H-pyrazol-5-amine (300 mg, 2.397 mmol), and the mixture was stirred at 62° C. for 18 h. The reaction mixture was concentrated in vacuo and the residue purified by column chromatography (Silica gel, gradient of 0 to 100% EtOAc/hexanes) to give 370 mg (56%) of product. LCMS E-S (M+H)=276.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 0.99-1.12 (m, 3 H), 1.46-1.54 (m, 3 H), 1.58-1.70 (m, 6 H), 1.82-1.96 (m, 2 H), 2.91-3.02 (m, 2 H), 4.51 (q, J=7.2 Hz, 2 H), 5.28-5.44 (m, 1 H), 7.58-7.68 (s, 1 H), 8.27-8.40 (s, 1 H)

Provenance & Evidence