C1C=CC2N(O)N=NC=2C=1.[CH3:11][CH2:12][N:13](C(C)C)[CH:14](C)[CH3:15].[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([OH:25])=O.C(NCC)C.CCN=C=NCCCN(C)C>C(Cl)Cl>[Br:20][C:21]1[CH:29]=[CH:28][CH:27]=[CH:26][C:22]=1[C:23]([N:13]([CH2:14][CH3:15])[CH2:12][CH3:11])=[O:25]HOBT (2.72 g, 10.08 mmol), DIPEA (3.52 mL, 20.16 mmol), 2-bromo benzoic acid (4.08 g, 10.08 mmol), and diethyl amine (2.08 mL, 10.08 mmol) were dissolved in DCM (100 mL) and stirred at r.t. for about 30 minutes. EDCI (3.86 g, 10.08 mmol) was added, and the mixture was stirred at r.t. for about 16 hours. The reaction was concentrated to an oil, and the oil was purified via column chromatography to give 2-bromo-N,N-diethyl-benzamide (3.35 g, 68%) as a yellow oil.
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