{5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester

Base Information

• Chemical Name: {5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester
• CAS No.: 875271-90-2
• Molecular Formula: C₃₇H₃₈N₂O₅S
• Molecular Weight: 622.785

Synonyms:{5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester

Chemical Property of {5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester

Chemical Property:

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Technology Process of {5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester

There total 9 articles about {5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester 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: 33.0%

[2-phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acid methyl ester (875271-85-5) + tert-butyl 4-bromobutylcarbamate (164365-88-2) → {5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester (875271-90-2)

Guidance literature:

With CsF/silica; In acetonitrile; for 18h; Inert atmosphere; Reflux;

Reference yield:

(2-phenylthiophen-3-yl)acetic acid methyl ester (875271-79-7) → {5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester (875271-90-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / AlCl₃ / CH₂Cl₂ / 20 °C

2: 96 percent / stannous chloride dihydrate / ethyl acetate / 0.5 h / Heating

3: 98 percent / Et₂NH; CuI / Pd(PPh₃)4 / 4 h / 20 °C

4: 61 percent / PdCl₂(PhCN)2 / dimethylformamide / 0.5 h / 80 °C

5: 33 percent Turnov_. / CsF on Celite / acetonitrile / 48 h / Heating

With copper(l) iodide; aluminium trichloride; diethylamine; cesium fluoride; tin(ll) chloride; bis(benzonitrile)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1: Friedel-Crafts reaction;

DOI:10.1016/j.bmc.2005.08.018

Reference yield:

(2-phenylthiophen-3-yl)acetic acid ethyl ester (875271-86-6) → {5-[1-(4-N-boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}acetic acid methyl ester (875271-90-2)

Guidance literature:

Multi-step reaction with 7 steps

1: KOH / methanol / 3 h / Heating

2: 3.3 g / HCl / 5 h / Heating

3: 74 percent / AlCl₃ / CH₂Cl₂ / 20 °C

4: 96 percent / stannous chloride dihydrate / ethyl acetate / 0.5 h / Heating

5: 98 percent / Et₂NH; CuI / Pd(PPh₃)4 / 4 h / 20 °C

6: 61 percent / PdCl₂(PhCN)2 / dimethylformamide / 0.5 h / 80 °C

7: 33 percent Turnov_. / CsF on Celite / acetonitrile / 48 h / Heating

With hydrogenchloride; potassium hydroxide; copper(l) iodide; aluminium trichloride; diethylamine; cesium fluoride; tin(ll) chloride; bis(benzonitrile)palladium(II) dichloride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 3: Friedel-Crafts reaction;

DOI:10.1016/j.bmc.2005.08.018

upstream raw materials:

[2-phenyl-5-(2-phenyl-1H-indole-6-carbonyl)thiophene-3-yl]acetic acid methyl ester

tert-butyl 4-bromobutylcarbamate

(2-phenylthiophen-3-yl)acetic acid methyl ester

(2-phenylthiophen-3-yl)acetic acid ethyl ester

Downstream raw materials:

[5-(1-{4-[(tert-butoxycarbonyl)amino]butyl}-2-phenyl-1H-indole-6-carbonyl)-2-phenylthiophene-3-yl]acetic acid

(4-{2-phenyl-6-[5-phenyl-4-(trityloxycarbamoyl-methyl)-thiophene-2-carbonyl]-indol-1-yl}-butyl)-carbamic acid tert-butyl ester

2-{5-[1-(4-N-Boc-aminobutyl)-2-phenyl-1H-indol-6-carbonyl]-2-phenylthiophen-3-yl}-N-hydroxyacetamide

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