Potassium Carbonate → HCID 25070234, compound

Participants

Reaction Steps

(S)-6-(Isopropyl(methyl)amino)-5,6,7,8-tetrahydronaphthalen-1-yl trifluoromethanesulfonate (184 mg, 0.524 mmol), 1,3,5-trimethyl-1H-pyrazole-4-boronic acid pinacol ester (142 mg, 0.602 mmol) and Pd(PPh3)4 (60 g, 0.0524 mmol) were added to a solution of K2CO3 (145 mg, 1.047 mmol) in a mixture of 1,2-dimethoxyethane (7 mL) and H2O (1 mL). The reaction mixture was purged with Ar (g) for 10 min, and warmed up to reflux. The reaction was completed in 4 h. It was allowed to reach room temperature, diluted with CH2Cl2 (20 mL) and acidified with HCl aqueous solution (10%, 30 mL). The organic layer was discarded, and the aqueous layer was taken to pH=9-10 with NaOH aqueous solution (10%). It was extracted with CH2Cl2 (3×20 mL), and the organic layer was dried over anhydrous Na2SO4, filtered and concentrated. The obtained crude was purified by flash chromatography on silica gel (5% Et3N/AcOEt), to afford 91 mg of the desired product (yellow oil, 56% yield).

Provenance & Evidence