Toluene → HCID 53862101, compound

Participants

Reaction Steps

1.00 g (2.43 mmol, 1.0 equiv) (±)-1-(1-cyclopentyl-3-ethyl-1H-indazol-6-yl)-1-phenyl-2-pyridin-4-yl-ethanol, 578 mg (3.04 mmol, 1.25 equiv) p-toluenesulfonic acid and 25 mL anhydrous toluene were placed in a flask fitted with a Dean-Stark trap and heated to reflux under nitrogen atmosphere. After 7 hours, the reaction mixture was cooled to room temperature and allowed to stir for 72 hours. The reaction mixture was diluted with 200 mL H2O and 100 mL 1N NaOH, and extracted 2×100 mL ethyl acetate. The organic extracts were combined, washed 1×50 mL each H2O, brine, and dried over Na2SO4. Filtration, concentration of filtrate and drying gave a yellow oil, which was purified on a silica gel column (2.5% CH3OH/CH2Cl2) to give 0.92 g (95%) of a white amorphous solid. A small sample was crystallized from ethyl acetate/hexanes to give 27 mg white needles: mp 134-1 36° C.; Anal. calcd for C27H27N3 : C, 82.41; H, 6.92; N, 10.68; Found: C, 82.31; H, 7.17; N, 10.80.

Provenance & Evidence