Реакция #2275711

Уравнение реакции

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

MeOH

K3PO4

4-methylphenyl boronic acid

→

desired compound

Выход 85.0%

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

Выход 85.0%

Растворители

1,4-dioxane

Условия реакции

Обработка

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

Методика

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]+.

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