Diisopropylethylamine → 2-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridine

Participants

Reaction Conditions

Reaction Steps

According to Scheme 3, Step 3: A mixture of 2-(4-bromothiazol-2-yloxy)pyridine (1.56 mmol, 400 mg), 1-(4-methoxybenzyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.87 mmol, 587 mg), PdCl2(dppf) (0.16 mmol, 127 mg) and N-ethyl-N-isopropylpropan-2-amine (3.11 mmol, 0.53 mL) in dioxane/water (1:1, 10 mL) was stirred at 150° C. for 1 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 cyclohexane/EtOAc (90:10 to 70:30) as eluent to yield 2-(4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-yloxy)pyridine (0.23 mmol, 83 mg, 9%) as an oil.

Provenance & Evidence