[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[C:11]1([NH:17][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[NH2:24])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C(N=C=NC(C)C)(C)C.C(N(CC)CC)C>ClCCl>[Br:1][C:2]1[CH:3]=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([NH:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[NH:17][C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)=[O:9]A mixture of 5-bromonicotinic acid (20.0 g, 99 mmol), N-phenyl-o-phenylenediamine (19.32 g, 105 mmol), diisopropylcarbodiimide (DIC) (26.5 g, 210 mmol), and triethylamine (TEA) (2.65 g, 27 mmol) in dichloromethane (DCM) (anhydrous, 350 mL) was heated to 50° C. and degassed with stirring overnight under argon. After cooling to room temperature (RT), the solids were filtered off. The filtrate was washed with water (2×200 mL), dried over sodium sulfate and loaded onto silica gel for purification by a flash chromatography column (gradient of 3% to 10% ethyl acetate in DCM) to yield Compound 1 (30.32 g of material; 83% yield).
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