Diisopropylethylamine → 2-(dimethylamino)-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)acetamide

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Reaction Steps

Into a 100 mL round bottom flask was placed 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzenamine 65 (438 mg, 2 mmol), dichloromethane (30 mL), diisopropylethylamine (517 mg, 4 mmol), and 2-(dimethylamino)acetyl chloride (267 mg, 2.2 mmol). The reaction was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure. Saturated aqueous sodium bicarbonate was added (20 mL), and the mixture was extracted with ethyl acetate (3×50 mL). The organic layers were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude was purified on a silica-gel column using 0 to 20% methanol in dichloromethane as the solvent gradient. The product fractions were collected and concentrated to afford the title compound 66 as an orange oil. Mass found by LC-MS(+): 305 (M+H); calc. for C16H25BN2O3: 304.19.

Provenance & Evidence