Potassium Carbonate → 2,3'-Diamino-biphenyl-4-carboxylic acid

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Reaction Steps

The general procedure described in Example 3 was used with 3-amino-4-chloro-benzoic acid (172 mg, 1.00 mmol), 3-aminophenylboronic acid (190 mg, 1.40 mmol), Pd(OAc)2 (2.2 mg, 0.010 mmol, 1 mol %), sodium 2-dicyclohexylphosphino-2′,6′-dimethoxybiphenyl-3′-sulfonate (10.0 mg, 0.020 mmol, 2 mol %), K2CO3 (552 mg, 4.00 mmol), water (3.0 mL), 12 h, 100° C. The product was isolated as a light brown oil (254 mg, 99%). 1H NMR (400 MHz, CDCl3/d4-MeOH) δ: 7.35 (m, 2H), 7.10 (t, 1H, J=7.6 Hz), 7.02 (d, 1H, J=8.0 Hz), 6.70-6.60 (m, 3H). 13C NMR (125 MHz, CDCl3/d4-MeOH) δ: 169.4, 146.6, 143.4, 139.4, 132.4, 129.9, 129.7, 129.0, 119.8, 118.9, 115.8, 115.5, 114.8. IR (neat, cm−1): 3419, 1645, 1016. EI-MS for C13H12N2O2: Theoretical [M+H]=229.0977. Found: 229.0982. Anal. Calcd for C13H12N2O2: C, 68.41; H, 5.30. Found: C, 68.29; H, 5.29.

Provenance & Evidence