Réaction #2275711

Équation de réaction

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

MeOH

K3PO4

4-methylphenyl boronic acid

→

desired compound

Rendement 85.0%

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

Rendement 85.0%

Solvants

1,4-dioxane

Conditions de réaction

Traitement

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

Mode opératoire

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]+.

Source