Diisopropylethylamine → 7-(3,4-dichlorophenyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline

Participants

Reaction Conditions

Reaction Steps

Synthesis of 7-(3,4-dichlorophenyl)-3-(4-methoxybenzyl)-6,7-dihydro-3H-benzo[f]pyrazolo[3,4-c]isoquinoline. To the mixture of (E)-4-(3,4-dichlorophenyl)-2-((dimethylamino)methylene)-3,4-dihydronaphthalen-1(2H)-one (0.20 g, 0.58 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine hydrochloride (0.14 g, 0.58 mmol) was added glacial acetic acid (5 mL) and Hunig's Base (0.4 mL). The mixture was heated at 110° C. for 1 hour, then transferred to microwave vial and heated at 220° C. for 90 minutes. The reaction mixture was evaporated and dissolved in dichloromethane (100 mL), washed with water (30 mL), brine (30 mL), dried over sodium sulfate and concentrated to dryness. The crude was purified by flash column chromatography (SiO2, 10% EtOAc in hexane) to give the pure desired product as a brown solid (0.15 g, 53%). M.p.=76-78° C.; 1H NMR (CDCl3, 400 MHz) δ 9.53 (d, J=8 Hz, 1H), 8.32 (s, 1H), 8.02 (s, 1H), 7.54 (t, J=6.8 Hz, 1H), 7.45 (t, J=8 Hz, 1H), 7.35-7.26 (m, 4H), 7.06 (d, J=8 Hz, 1H), 6.96 (d, J=8 HZ, 1H), 6.843 (d, J=7.2 Hz, 2H), 4.28 (t, J=8 Hz, 1H), 4.17 (s, 2H), 3.77 (s, 3H), 3.29-3.26 (m, 2H); LCMS: 486 [M+1].

Provenance & Evidence