Benzene → Ethyl 6-(4-bromophenyl)-1-(1-methylethyl)-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

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Reaction Steps

The title compound was prepared in the same manner as described for intermediate 61 using ethyl 4-(4-bromophenyl)-2,4-dioxobutanoate (956 mg, 3.20 mmol), benzene (10 mL), 1-(1-methylethyl)-1H-pyrazol-5-amine (400 mg, 3.20 mmol), and acetic acid (4 mL). The crude product was purified using column chromatography (Silica gel, eluent: 0 to 100% EtOAc/hexanes) to give 1.1 g (89%) of product. LCMS E-S (M+H)=388.1. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.49-1.57 (t, J=67.2 Hz, 3H), 1.63-1.74 (d, J=6.8 Hz 6H), 4.56 (q, J=7.2 Hz, 2H), 5.46 (spt, J=6.7 Hz, 1H), 7.65-7.71 (m, 2H), 8.04-8.15 (m, 2H), 8.21 (s, 1H), 8.42 (s, 1H).

Provenance & Evidence