Diisopropylethylamine → HCID 86665172, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 5, Step 4: A mixture of 1-(4-methoxybenzyl)-4-iodo-N-methoxy-N-methyl-1H-pyrazole-3-carboxamide (0.59 mmol, 238 mg), 2-(6-methylpyridin-2-yloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (0.49 mmol, 157 mg), PdCl2(dppf) (49 μmol, 40 mg) and N-ethyl-N-isopropylpropan-2-amine (0.99 mmol, 0.17 mL) in dioxane/water (1:1, 3.3 mL) was stirred at 120° C. for 30 minutes 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 1-(4-methoxybenzyl)-N-methoxy-N-methyl-4-(2-(6-methylpyridin-2-yloxy)thiazol-4-yl)-1H-pyrazole-3-carboxamide (99 μmol, 46 mg, 15%) as an oil.

Provenance & Evidence