Boron tribromide → HCID 20094644, compound

Participants

Reaction Steps

1-(4-Methoxyphenyl)-7-[(naphthyl)methyl]-4,5,6,7-tetrahydro-1H-indazole-3-carboxaldehyde (CP 325, 3.44 g, 8.68 mmol) and 26 mL of a 1.0M solution of BBr3 in CH2Cl2 (26 mmol) were combined and stirred at room temperature for 3 h. Additional CH2Cl2 was added and the solution was washed with water and brine. The mixture was concentrated and purified by MPLC using a solvent gradient ranging from 20-25% EtOAc:hexanes to give 0.40 g (12%) of the title compound as a white solid, m.p. >260° C.; 1H NMR (DMSO-d6, 300 MHz) 1.50 (m, 2H), 1.75 (m, 1H), 1.95 (m, 1H), 2.60 (m, 1H), 2.77 (t, 1H, J=12.7), 2.94 (broad d, 1H, J=13.6), 3.06 (broad d, 1H, J=10.8), 3.25 (m, 1H), 6.90 (d, 1H, J=8.5), 7.09 (d, 2H, J=8.7), 7.21 (d, 1H, J=6.5), 7.28 (t, 1H, J= 7.1), 7.4 (t, 1H, J=7.6), 7.47 (t, 1H J=7.4), 7.54 (d, 2H , J=8.7), 7.76 (d, 1H, J=8.2), 7.87 (d, 1H, J=7.9); IR (KBr) 3100 (broad), 1696, 1519 cm-1 ; MS (DCI) m/z 383 (base), 241. Anal. Calcd. for C26H26N2O2 : C, 78.63; H, 6.58; N, 7.03. Found: C, 78.23; H, 6.53; N, 6.99.

Provenance & Evidence