Picolinic acid → HCID 57941482, compound

Participants

Reaction Steps

A mixture of (4S,7R)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (Intermediate 19; 412 mg, 2 mmol), 3-iodo-methoxy-benzene (264 μL, 2.2 mmol), copper(I) iodide (19 mg, 0.1 mmol), picolinic acid (49 mg, 0.4 mmol), and potassium bicarbonate (280 mg, 2.8 mmol) in N,N-dimethylformamide (10 mL) was irradiated in a microwave oven at 220° C. for 30 min. The reaction mixture was diluted with 0.1 M HCl (200 mL) and then extracted with ethyl acetate (200 mL). The organic layer was washed with 0.1 M HCl, 0.25 M NaOH, and brine, then dried (magnesium sulfate), filtered, evaporated and purified using an ISCO system, eluting with 5-60% ethyl acetate/dichloromethane to give a tan semi-solid. This was dissolved in ethyl acetate (30 mL) and washed with 0.1 M HCl (30 mL), then dried, filtered, evaporated and triturated with petroleum ether to give (4S,7R)-2-(3-methoxy-phenyl)-1,7,8,8-tetramethyl-1,2,4,5,6,7-hexahydro-4,7-methano-indazol-3-one (107 mg, 20%) as a white solid. ES(+)-MS (M+H) 313.

Provenance & Evidence