反応 #2275711

反応方程式

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

MeOH

K3PO4

4-methylphenyl boronic acid

→

desired compound

収率 85.0%

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

収率 85.0%

溶媒

1,4-dioxane

反応条件

後処理

1. 1
   その他The solvents are then removed under reduced pressure
2. 2
   その他the solid which remains is partitioned between CH2Cl2 and 1M K2CO3
3. 3
   その他The aqueous phase is removed
4. 4
   洗浄the organic phase washed with H2O, sat. NaCl
5. 5
   乾燥dried (MgSO4)
6. 6
   ろ過filtered
7. 7
   濃縮concentrated under reduced pressure
8. 8
   その他The crude material is purified over silica (EtOAc:heptane gradient 1:4 to 3:7)

実験手順

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]+.

出典