반응 #2275711

반응 방정식

[(4-iodo-pyridine-2-carbonyl)-amino]-acetic acid methyl ester

MeOH

K3PO4

4-methylphenyl boronic acid

→

desired compound

수율 85.0%

[(4-(4-methylphenyl)pyridine-2-carbonyl)amino]-acetic acid methyl ester

수율 85.0%

용매

1,4-dioxane

반응 조건

후처리

1. 1
   기타The solvents are then removed under reduced pressure
2. 2
   기타the solid which remains is partitioned between CH2Cl2 and 1M K2CO3
3. 3
   기타The aqueous phase is removed
4. 4
   세척the organic phase washed with H2O, sat. NaCl
5. 5
   건조dried (MgSO4)
6. 6
   여과filtered
7. 7
   농축concentrated under reduced pressure
8. 8
   기타The crude material is purified over silica (EtOAc:heptane gradient 1:4 to 3:7)

실험 절차

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 (1H, dd, J=5.1, 0.7 Hz), 8.55 (1H, t, J=4.8 Hz), 8.43-8.44 (1H, m), 8.43 (1H, s), 7.66 (1H, dd, J=5.1, 1.8 Hz), 7.63 (2H, d, J=8.4 Hz), 7.32 (2H, d, J=8.1 Hz), 4.31 (1H, d, J=5.9 Hz), 3.81 (2H, s), 2.43 (3H, s). HPLC-MS: m/z 285 [M+H]+.

출처