تفاعل #52265

معادلة التفاعل

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

benzyl isocynate

→

title compound

المردود 42.0%

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

المردود 42.0%

المذيبات

acetonitrile

ظروف التفاعل

المعالجة

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

الإجراء التجريبي

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).

المصدر