Diisopropylethylamine → HCID 178425695, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 4: A mixture of 2-(4-bromothiazol-2-yloxy)-6-methylpyridine (0.37 mmol, 100 mg), 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.44 mmol, 92 mg), Pd (dppf) (37 μmol, 30 mg) and N-ethyl-N-isopropylpropan-2-amine (0.74 mmol, 0.13 mL) in dioxane/water (1:1, 2.5 mL) was stirred at 120° C. for 1 hour under microwave conditions. To complete the reaction, PdCl2(dppf) (37 μmol, 30 mg) and 3-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.44 mmol, 92 mg) were added and the reaction mixture was stirred at 120° C. for 1.5 hour under microwave conditions. The reaction mixture was filtered through a pad of celite and was washed with DCM. The organic phase was washed with water, was dried over MgSO4, was filtered and was concentrated under reduced pressure. The crude mixture was purified by flash chromatography over silica gel using DCM/EtOH/NH3 (100:0:0 to 93:6.4:0.6) as eluent to yield 4-(3-methyl-1H-pyrazol-4-yl)-2-(6-methylpyridin-2-yloxy)thiazole (95 μmol, 26 mg, 26%) as an orange solid.

Provenance & Evidence