反応 #52265

反応方程式

methyl 3-[5-(aminopropoxy)indolyl]propanoate

benzyl isocynate

→

title compound

収率 42.0%

Methyl 3-[5-(3-{[benzylamino]carbonylamino}propoxy)indolyl]propanoate

収率 42.0%

溶媒

acetonitrile

反応条件

後処理

1. 1
   その他After evaporating the solvent in vacuo
2. 2
   その他the residue was purified by flash column chromatography on silica gel (methylene chloride to 5% ethyl acetate in methylene chloride)

実験手順

To the solution of methyl 3-[5-(aminopropoxy)indolyl]propanoate (140 mg, 0.5 mmol), as prepared in the preceding step, in acetonitrile (10 mL) was added benzyl isocynate (135 mg, 1.0 mmol), and the mixture was stirred at ambient temperature overnight. After evaporating the solvent in vacuo, the residue was purified by flash column chromatography on silica gel (methylene chloride to 5% ethyl acetate in methylene chloride) to give the title compound as a white solid (85 mg, 42%). 1H-NMR (400 MHz, CDCl3) δ 7.28 (m, 5H), 7.20 (d, J=8.9 Hz, 1H), 7.10 (d, J=2.8 Hz, 1H), 7.05 (d, J=2.5 Hz, 1H), 6.81 (dd, J=8.8, 2.5 Hz, 1H), 6.38 (d, J=2.9 Hz, 1H), 4.66 (br s, 2H), 4.41 (t, J=6.8 Hz, 2H), 4.35 (d, J=5.7 Hz, 2H), 4.06 (t, J=5.8 Hz, 2H), 3.66 (s, 3H), 3.43 (q, J=6.2 Hz, 2H), 2.81 (t, J=6.8 Hz, 2H), 1.99 (t, J=6.1, 2H).

出典