(E)-5-(2-Methyl-4-nitro-5-(2-(pyrrolidin-1-yl)vinyl)phenoxy)pyrimidine → 6-Methyl-5-(pyrimidin-5-yloxy)-1H-indole
反応式
[CH3:1][C:2]1[CH:14]=[C:13]([N+]([O-])=O)[C:12](/[CH:18]=[CH:19]/[N:20]2CCCC2)=[CH:11][C:3]=1[O:4][C:5]1[CH:6]=[N:7][CH:8]=[N:9][CH:10]=1>CO.[Pd]>[CH3:1][C:2]1[CH:14]=[C:13]2[C:12]([CH:18]=[CH:19][NH:20]2)=[CH:11][C:3]=1[O:4][C:5]1[CH:10]=[N:9][CH:8]=[N:7][CH:6]=1参加物
4
実験手順
A red, heterogeneous solution of (E)-5-(2-methyl-4-nitro-5-(2-(pyrrolidin-1-yl)vinyl)phenoxy)pyrimidine (0.963 g, 2.95 mmol) and 10% Pd/C (0.314 g, 0.295 mmol) in methanol (49.2 mL) was hydrogenated overnight. The reaction was flushed with nitrogen, filtered through a pad of CELITE®, and rinsed with MeOH. The filtrate was concentrated in vacuo to give a residue which was purified by flash chromatography using an ISCO 40 g column eluting with 0-5% MeOH/CH2Cl2. Appropriate fractions were collected and concentrated in vacuo to the desired product (0.3082 g, 1.37 mmol, 46.4%) as a light yellow solid.