Sodium Carbonate → 1-Cyclopentyl-3-ethyl-6-(2-thienyl)-1H-indazole

Participants

Reaction Steps

A solution of 76 mg (0.598 mmol, 1.2 equiv) thiophene-2-boronic acid in 0.5 mL methanol was added to a room temperature suspension of 146 mg (0.498 mmol, 1.0 equiv) 6-bromo-1-cyclopentyl-3-ethyl-1H-indazole and 17 mg (0.0149 mmol, 0.03 equiv) Pd(PPh3)4in 2 mL toluene and 0.5 mL 2M aqueous Na2CO3. The mixture was heated to reflux for 4 h, then cooled to room temperature. The reaction mixture was diluted with 50 mL ethyl acetate, washed 1×10 mL each H2O, brine, and dried over MgSO4. The crude product was purified on a silica gel column (3% ethylacetate/hexanes, flash) to give 81 mg (55%) of a clear oil, which crystalized onstanding: mp 60-64° C.; HRMS calcd for C18H20N2S+H: 297.1427. Found: 297.1484.

Provenance & Evidence