Methanol → [(4-(4-Methylphenyl)pyridine-2-carbonyl)amino]-acetic acid methyl ester

Participants

Reaction Conditions

Reaction Steps

To a degassed solution of [(4-iodo-pyridine-2-carbonyl)-amino]-acetic acid methyl ester, 23, (0.150, 0.47 mmol) in 1,4-dioxane (4 mL) and MeOH (2 mL) is added K3PO4 (0.109 mg, 0.52 mmol), Pd(dppf)Cl2 (0.038 g, 0.047 mmol) and 4-methylphenyl boronic acid (0.064 g, 0.47 mmol). The reaction is heated to 70° C. in a sealed tube under N2 for 16 hours. The solvents are then removed under reduced pressure and the solid which remains is partitioned between CH2Cl2 and 1M K2CO3. The aqueous phase is removed and the organic phase washed with H2O, sat. NaCl, dried (MgSO4), filtered and concentrated under reduced pressure. The crude material is purified over silica (EtOAc:heptane gradient 1:4 to 3:7) to afford 0.113 g (85% yield) of the desired compound. 1H NMR (400 MHz, CDCl3) δ ppm 8.60 (1 H, dd, J=5.1, 0.7 Hz), 8.55 (1 H, t, J=4.8 Hz), 8.43-8.44 (1 H, m), 8.43 (1 H, s), 7.66 (1 H, dd, J=5.1, 1.8 Hz), 7.63 (2 H, d, J=8.4 Hz), 7.32 (2 H, d, J=8.1 Hz), 4.31 (1 H, d, J=5.9 Hz), 3.81 (2 H, s), 2.43 (3 H, s). HPLC-MS: m/z 285 [M+H]+.

Provenance & Evidence