Diisopropylethylamine → 2-ethyl-4-methyl-N-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)oxazole-5-carboxamide

Participants

Reaction Steps

To a stirred solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) aniline (360 mg, 1.643 mmol) in anhydrous DMF (8.2 mL) was added 2-ethyl-4-methyloxazole-5-carboxylic acid (306 mg, 1.972 mmol), followed by DIPEA (0.86 mL, 4.93 mmol) and the mixture was stirred at room temperature for 10 minutes. HATU (750 mg, 1.972 mmol) was added and the mixture was stirred at room temperature for 16 hour. The mixture was taken up in 1:1 mixture of brine and water (40 mL) and extracted with EtOAc (60 mL). The organic portion was dried over sodium sulfate, filtered and concentrated to afford a brown oil, which was purified by flash column chromatography to afford the title compound (305 mg, 52% yield) as a white solid. LC/MS, ESI-MS (+): 357.1, RT: 1.35 (Condition E).

Provenance & Evidence