N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide

Base Information

Chemical Name:N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide
CAS No.:581065-66-9
Molecular Formula:C₄₆H₄₈N₂O₄S
Molecular Weight:724.964
Hs Code.:

Synonyms:N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide

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Chemical Property of N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide

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Technology Process of N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide

There total 14 articles about N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 80.0%

: 581065-57-8
4,4,5,5-tetramethyl-2-[3-(2-(1-piperidinyl)ethyloxy)phenyl]-[1,3,2]-dioxaborolane

: 581065-65-8
6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-3-[(diethylamino)carbonyl]benzo[b]thiophen-4-yl trifluoromethanesulfonate

: 581065-66-9
N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide

Guidance literature:: With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,2-dimethoxyethane; for 3h; Heating;
DOI:10.1021/jo034325k

Reference yield:

: 591-20-8
3-Bromophenol

: 581065-66-9
N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide

Guidance literature:: Multi-step reaction with 4 steps

1.1: 69 percent / aq. NaOH / 1 h / Heating

2.1: n-BuLi / tetrahydrofuran; hexane / 0.5 h / -78 °C

2.2: tetrahydrofuran; hexane / -78 - 20 °C

3.1: 2.45 g / tetrahydrofuran; hexane / 12 h

4.1: 80 percent / Pd(PPh₃)4; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 3 h / Heating

With sodium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; sodium carbonate; In tetrahydrofuran; 1,2-dimethoxyethane; hexane; 4.1: Suzuki-Miyaura cross-coupling reaction;
DOI:10.1021/jo034325k

Reference yield:

: 13246-46-3
2,4-dibenzyloxybenzaldehyde

: 581065-66-9
N,N-diethyl 6-(benzyloxy)-2-[4-(benzyloxy)phenyl]-4-[3-(2-piperidinoethoxy)phenyl]benzo[b]thiophene-3-carboxamide

Guidance literature:: Multi-step reaction with 8 steps

1.1: 41 percent / LDA / tetrahydrofuran; hexane / 8 h / -78 - 20 °C

2.1: MeSO₃H / CH₂Cl₂ / 1.5 h / 0 - 20 °C

3.1: 4.31 g / aq. HCl / ethanol / Heating

4.1: HNEt₂ / acetic acid / 12 h / Heating

4.2: 69 percent / acetonitrile / 12 h / Heating

5.1: 63 percent / DDQ / toluene / 4 h / Heating

6.1: 82 percent / 9-Br-BBN / CH₂Cl₂ / 6 h / -78 - 20 °C

7.1: 85 percent / NEt₃ / CH₂Cl₂ / 1.5 h / 0 °C

8.1: 80 percent / Pd(PPh₃)4; aq. Na₂CO₃ / 1,2-dimethoxy-ethane / 3 h / Heating

With hydrogenchloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; methanesulfonic acid; 9-Br-BBN; sodium carbonate; diethylamine; triethylamine; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium diisopropyl amide; In tetrahydrofuran; 1,2-dimethoxyethane; ethanol; hexane; dichloromethane; acetic acid; toluene; 8.1: Suzuki-Miyaura cross-coupling reaction;
DOI:10.1021/jo034325k