Trifluoroacetic acid → HCID 59490674, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of 6,7,8,9-tetrahydro-5H-benzo[7]annulen-5-one (8.5 g, 39.5 mmol) and 1-(4-methoxybenzyl)-1H-pyrazol-5-amine (8.2 g, 44.47 mmol) was added trifluoroacetic acid (4.25 mL, 54.3 mmol). The reaction mixture was heated at 100° C. for 24 hours. On completion of the reaction, the solvent was removed under reduced pressure and the crude product was purified by flash column chromatography (SiO2, gradient from 5% EtOAc in hexanes to 30% EtOAc in hexanes) to give the desired product (4.2 g, 30%) as an off-colored solid. 1H NMR (CDCl3, 400 MHz) δ: 7.97 (s, 1H), 7.85 (s, 1H), 7.79 (d, J=7.2 Hz, 1H), 7.46-7.44 (m, 1H), 7.38 (d, J=7.6 Hz, 2H), 7.28 (s, 1H), 7.26 (s, 1H), 6.84 (d, J=7.6 Hz, 2H), 5.69 (s, 2H), 3.76 (s, 3H), 2.59 (q, J=6.0 Hz, 4H), 2.21 (quintet, J=7.2 Hz, 2H); LCMS [M+H]: 356.

Provenance & Evidence