Hydrochloric Acid → HCID 15229930, compound

Participants

Reaction Conditions

Reaction Steps

1-(4-Fluorophenyl)-7-[(1-naphthyl)methyl]-4,5,6,7-tetrahydro-1H-indazole-3-methanol (CP 366, 0.864 mmol, 0.334 g) and 0.077 mL (1.35 mmol, 0.085 g) of pyridine were dissolved in 3 mL of CH2Cl2 and cooled to 0° C. under N2Acetyl chloride (1.08 mmol, 0.107 g, 0.109 mL) was added and the solution was stirred at 0° C. for 2 h. Water and 2N aqueous HCl were added and the mixture was extracted with ether. The organic layer was washed with saturated aqueous NaHCO3 and brine, dried over Na2SO4 and concentrated to give 0.350 g (94%) of the title compound as an off-white solid. Recrystallization from EtOAc:hexanes afforded 0.084 g of analytically pure white solid, m.p. 142°-144° C.; 1H NMR (CDCl3, 300 MHz) 1.5-2.1 (complex, 4H), 2.13 (s, 3H), 2.52 (m, 1H), 2.71 (m, 1H), 2.84 (dd, 1H, J=11.1, 13.8), 3.14 (dd, 1H, J=4.1, 13.8), 3.38 (m, 1H), 5.16 (s, 2H), 7.10 (d, 2H, J=8.0), 7.2-7.5 (complex, 7H). 7.68 (d, 1H, J=8.2), 7.79 (d, 1H, J=8.0); IR (KBr) 1733, 1516, 1222 cm-1 ; MS (DCI) m/z 429 (base), 369. Anal. Calcd. for Calcd. for C27H25FN2O2 : C, 75.68; H, 5.88; N, 6.54. Found: C, 75.46; H, 5.83; N, 6.29.

Provenance & Evidence