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2-amino-6-bromobenzonitrile is a versatile building block that can be used to create a range of compounds, such as 4'-methoxy-3-(phenylethynyl)-[1,1'-biphenyl]-2-carbonitrile, etc.
Substituted phenylboronic acid (6 mmol), 2-amino-6-bromobenzonitrile (5 mmol), PdCl2(PPh3)2 (35.0 mg, 0.05 mmol) and Cs2CO3 (4.89 g, 15.0 mmol) were added in CH3CN (20 mL) and H2O (1.6 mL). The reaction mixture was stirred at 80 she℃ under an argon atmosphere for 12 h. After the reaction, the mixture was cooled to room temperature and extracted with EtOAc (40 × 3 mL). The combined organic phase was washed with brine (40 mL), and dried over anhydrous MgSO4. The solvent was removed under vacuum to give the crude product C without further purification.

[1] Zhou, Nengneng et al. “TBPB-initiated cascade cyclization of 3-arylethynyl-[1,1′-biphenyl]-2-carbonitriles with sulfinic acids: access to sulfone-containing cyclopenta[gh]phenanthridines?.” Organic & Biomolecular Chemistry 9 (2020): 1733–1737.