methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

Base Information

Chemical Name:methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate
CAS No.:900152-54-7
Molecular Formula:C₂₇H₃₄BrNO₅Si
Molecular Weight:560.56
Hs Code.:

Synonyms:methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

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Chemical Property of methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

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Technology Process of methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

There total 8 articles about methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate 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: 56.0%

: 900152-51-4
methyl 4,5-dibromo-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

: 186837-48-9
3-(tert-butyldimethylsilyloxy)-4-methyloxyphenyl iodide

: 900152-54-7
methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

Guidance literature:: methyl 4,5-dibromo-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate; With phenyllithium; In tetrahydrofuran; diethyl ether; cyclohexane; at -78 ℃; for 0.2h;

With zinc(II) chloride; In tetrahydrofuran; diethyl ether; cyclohexane; at -78 ℃; for 0.0833333h;

3-(tert-butyldimethylsilyloxy)-4-methyloxyphenyl iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; diethyl ether; cyclohexane; at -78 - 66 ℃; for 96h;
DOI:10.1016/j.bmc.2006.02.018

Reference yield:

: 1193-62-0
methyl Pyrrole-2-carboxylate

: 900152-54-7
methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: 75 percent / sodium hydroxide / H₂O; CH₂Cl₂ / 16 h / 18 °C

2.1: 83 percent / N-bromosuccinimide / dimethylformamide / 16 h / 0 - 18 °C

3.1: phenyllithium / cyclohexane; diethyl ether; tetrahydrofuran / 0.2 h / -78 °C

3.2: zinc chloride / cyclohexane; diethyl ether; tetrahydrofuran / 0.08 h / -78 °C

3.3: 56 percent / Pd(PPh₃)4 / cyclohexane; diethyl ether; tetrahydrofuran / 96 h / -78 - 66 °C

With sodium hydroxide; N-Bromosuccinimide; phenyllithium; In tetrahydrofuran; diethyl ether; dichloromethane; cyclohexane; water; N,N-dimethyl-formamide; 3.3: Negishi cross-coupling;
DOI:10.1016/j.bmc.2006.02.018

Reference yield:

: 613-70-7
2-methoxyphenyl acetate

: 900152-54-7
methyl 4-bromo-5-{3-[tert-butyl(dimethyl)silyloxy]-4-methoxyphenyl}-1-(4-methoxybenzyl)-1H-pyrrole-2-carboxylate

Guidance literature:: Multi-step reaction with 4 steps

1.1: 73 percent / silver trifluoroacetate; iodine / CHCl₃ / 5 h / 0 - 18 °C

2.1: 99 percent / potassium carbonate / methanol / 16 h / 18 °C

3.1: 84 percent / imidazole / dimethylformamide / 16 h / 0 - 18 °C

4.1: phenyllithium / cyclohexane; diethyl ether; tetrahydrofuran / 0.2 h / -78 °C

4.2: zinc chloride / cyclohexane; diethyl ether; tetrahydrofuran / 0.08 h / -78 °C

4.3: 56 percent / Pd(PPh₃)4 / cyclohexane; diethyl ether; tetrahydrofuran / 96 h / -78 - 66 °C

With 1H-imidazole; iodine; silver trifluoroacetate; potassium carbonate; phenyllithium; In tetrahydrofuran; methanol; diethyl ether; chloroform; cyclohexane; N,N-dimethyl-formamide; 4.3: Negishi cross-coupling;
DOI:10.1016/j.bmc.2006.02.018