Реакция #76651

ord-562cb8c395cf4619985de4d69aac1107

Уравнение реакции

O=C(NCCCc1ccc(Br)cc1)OCc1ccccc1
N-[3-(4-Bromophenyl)propyl](phenylmethoxy)carboxamide
B1C2CCCC1CCC2
9-BBN
[Na+].[OH-]
sodium hydroxide
C=CCNC(=O)OCc1ccccc1
(phenylmethoxy)-N-eth-2-enylcarboxamide
C=CCNC(=O)OCc1ccccc1
(phenylmethoxy)-N-prop-2-enylcarboxamide
O=C(NCCCc1ccc(CCNC(=O)OCc2ccccc2)cc1)OCc1ccccc1
(phenylmethoxy)-N-[3-(4-{2-[(phenylmethoxy)carbonylamino]ethyl}phenyl)propyl]carboxamide
Выход 35.4%

Растворители

Условия реакции

Подробные условия
See reaction.notes.procedure_details.

Методика

N-[3-(4-Bromophenyl)propyl](phenylmethoxy)carboxamide (1.5 g, 4.3 mmol), (phenylmethoxy)-N-eth-2-enylcarboxamide (0.92 g, 5.17 mmol, prepared in example 8), 9-BBN-dimer (0.84 g, 3.45 mmol), [1,1′bis(diphenylphosphino)-ferrocene] dichloropalladium (11), PdCl2(dppf), (0.175 9, 0.22 mmol), 3N sodium hydroxide (3 mL), and pH=7 buffer hydrogen peroxide (2:1, 10 mL) were combined in a manner analogous to the procedure described in example 6 to provide the intermediate title compound, (phenylmethoxy)-N-[3-(4-{2-[(phenylmethoxy)carbonylamino]ethyl}phenyl)propyl]carboxamide, (0.68 g, 35%). Electron spray M.S. 447 (M*+H).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US06703425B2uspto-grants-2004_03