Dimethylformamide → HCID 58019992, compound

Participants

Reaction Steps

To a solution of I-168 (138 mg, 0.500 mmol) and 3,5-dimethyl-isoxazole-4-boronic acid (70 mg, 0.500 mmol) in dimethyl formamide (5 mL) were added palladium(0) bis(dibenzylideneacetone (14 mg, 0.025 mmol), triphenylphosphine (13 mg, 0.0500 mmol) and 1 M aqueous sodium carbonate (1.5 mL, 1.5 mmol). The resultant suspension was stirred at 85° C. for 72 h. The reaction was concentrated under reduced pressure, diluted with ethyl acetate (10 mL), washed with water (3×10 mL) and brine, dried over sodium sulfate, filtered, and the solvent removed under reduced pressure. The crude residue was purified by silica gel preparatory thin layer chromatography eluting with 1:1 hexanes and dichloromethane to afford 16.2 mg (10%) of P-062. 1H NMR (400 MHz, CDCl3) 2.11 (s, 3H), 2.31 (s, 3H), 3.64 (s, 2H), 3.79 (s, 3H), 5.98 (s, 2H), 6.80-6.94 (m, 3H), 6.94-7.05 (m, 3H) ppm. LCMS=100% purity. APCI (+)=338.10 (M+1).

Provenance & Evidence