反应详情

温度

0 °C

To a solution of 3,4-diamino-5-methyl-benzonitrile (2.00 g, 13.6 mmol) in MeOH (40 mL) was added 4-iodo-2-methoxy-pyridine-3-carbaldehyde (3.6 g, 13.6 mmol) in MeOH (20 mL) at 0° C. The resulting slurry was stirred at 0° C. for 1 h. Iodine (1.73 g, 8.8 mmol) in MeOH (10 mL) was added dropwise via a dropping funnel to the reaction mixture at 0° C. The reaction mixture was stirred at room temperature for 14 h. After removal of MeOH, the residue was diluted with saturated Na2S2O3 and extracted with EtOAc. The combined organic layers were washed with water and brine, dried over Na2SO4. The crude product was purified by flash column chromatography (3% MeOH/CH2Cl2) to yield the title compound (1.81 g, 46%). 1H NMR (300 MHz, CDCl3) δ 7.90 (1H, s), 7.49 (1H, d, J=5.4 Hz), 7.46 (1H, s), 7.41 (1H, d, J=5.3 Hz), 3.78 (3H, s), 2.68 (3H, s). LCMS (M+H)+ m/z 391 (t=1.27 min.).

1. stirringThe reaction mixture was stirred at room temperature for 14 h
2. customAfter removal of MeOH
3. additionthe residue was diluted with saturated Na2S2O3
4. extractionextracted with EtOAc
5. washThe combined organic layers were washed with water and brine
6. dry with materialdried over Na2SO4
7. customThe crude product was purified by flash column chromatography (3% MeOH/CH2Cl2)