2-Isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane → HCID 66889350, compound

Participants

Reaction Conditions

Reaction Steps

According to Scheme 5, Step 3: At −78° C., under a nitrogen atmosphere, BuLi (3.69 mmol, 1.48 mL) was added dropwise to a solution of 2-(4-bromothiazol-2-yloxy)-6-methylpyridine (1.68 mmol, 455 mg) in Et2O (17 mL). After 5 minutes of stirring at −78° C., 2-isopropoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane (3.69 mmol, 0.75 mL) was added and the resulting mixture was stirred at room temperature for 20 minutes. The reaction was quenched with a NH4Cl saturated aqueous solution and was extracted with EtOAc. The combined organic phases were dried over MgSO4, filtered and concentrated under reduced pressure. The crude mixture was purified by flash chromatography over silica gel using cyclohexane/EtOAc (70:30 to 30:70) as eluent to yield 2-(6-methylpyridin-2-yloxy)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)thiazole (0.49 mmol, 157 mg, 29%).

Provenance & Evidence