benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate

Base Information

• Chemical Name: benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate
• CAS No.: 764665-03-4
• Molecular Formula: C₁₈H₂₀BrNO₄
• Molecular Weight: 394.265

Synonyms:benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate

Chemical Property of benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate

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Technology Process of benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate

There total 1 articles about benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate 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:

N-(Benzyloxycarbonyloxy)succinimide (13139-17-8) + 2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine (63375-81-5) → benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate (764665-03-4)

Guidance literature:

With sodium hydroxide; In 1,4-dioxane; at 20 ℃; for 12h;

DOI:10.1002/ejoc.200400213

Reference yield: 94.0%

phenylboronic acid (98-80-6) + benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate (764665-03-4) → benzyl [2-(4,5-dimethoxybiphenyl-2-yl)ethyl]carbamate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In diethyl ether; N,N-dimethyl-formamide; at 140 ℃; for 0.166667h; Further Variations:; Solvents; Reagents; Temperatures; Product distribution; microwave irradiation;

DOI:10.1002/ejoc.200400213

Reference yield: 90.0%

4-pyridylboronic acid (1692-15-5) + benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate (764665-03-4) → benzyl [2-(4,5-dimethoxy-2-pyridin-4-ylphenyl)ethyl]carbamate

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; caesium carbonate; In water; N,N-dimethyl-formamide; at 150 ℃; for 0.25h; microwave irradiation;

DOI:10.1002/ejoc.200400213

upstream raw materials:

N-(Benzyloxycarbonyloxy)succinimide

2-(2-bromo-4,5-dimethoxyphenylphenyl)ethan-1-amine

Downstream raw materials:

benzyl [2-(2'-formyl-4,5-dimethoxybiphenyl-2-yl)ethyl]carbamate

Refernces

Generation of a small library of highly electron-rich 2-(hetero)aryl- substituted phenethylamines by the Suzuki-Miyaura reaction: A short synthesis of an apogalanthamine analogue

10.1002/ejoc.200400213

The research focuses on the synthesis of a small library of highly electron-rich 2-aryl and 2-heteroaryl phenethylamines (PEAs) using the Suzuki-Miyaura cross-coupling reaction, which is enhanced by microwave irradiation for improved reaction yield and speed. The study commenced with the synthesis of benzyl [2-(2-bromo-4,5-dimethoxyphenyl)ethyl]carbamate from 2-(3,4-dimethoxyphenyl)ethylamine, followed by its coupling with various boronic acids to generate the PEAs. The reactions were optimized using sodium hydrogencarbonate as the base and tetrakis(triphenylphosphane)palladium(0) as the catalyst, with the mixture of N,N-dimethylformamide and water as the solvent. The synthesized compounds were characterized by 1H and 13C NMR spectroscopy, and low-resolution mass spectrometry (LR-MS) to confirm their structures and purities. The research also successfully extended this methodology to synthesize an apogalanthamine analogue, a complex natural product with significant biological activities, showcasing the versatility and efficacy of the developed synthetic strategy.

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