4-Iodotoluene → HCID 66661508, compound

Participants

Reaction Conditions

Reaction Steps

5-(1H)indazole carboxylic acid methyl ester (302.1 mg, 1.715 mmol), 4-iodotoluene (457.2 mg, 2.097 mmol), copper iodide (17.4 mg, 0.091 mmol), trans-1,2-bis(methylamino)cyclohexane (275 μl, 0.348 mmol), and tribasic potassium phosphate (771.4 mg, 3.63 mmol) were dissolved in toluene (1700 μl) at 25° C. under Ar. The reaction mixture was warmed to 120° C. and allowed to stir for 14 h. The reaction was stopped, cooled to room temperature, quenched by addition of saturated aqueous ammonium chloride (10 mL), and extracted with ethyl acetate (3×10 mL). The combined organic phases were washed with saturated aqueous sodium chloride (1×10 mL), dried (sodium sulfate), filtered, and the solvent evaporated under reduced pressure. The crude product was purified by flash chromatography (RediSep SiO2, 40 g column) on a CombiFlash Rf purification system eluting with ethyl acetate-hexanes (0-65%). The title compound (330.5 mg, 1.241 mmol, 72.4% yield) was recovered as a light yellow/white solid. LC-MS: [M+1]=267.3.

Provenance & Evidence