2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester

Base Information

• Chemical Name: 2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester
• CAS No.: 88839-92-3
• Molecular Formula: C₃₆H₃₃N₅O₇S
• Molecular Weight: 679.753

Synonyms:2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester

Chemical Property of 2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester

There total 12 articles about 2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.0^2,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic 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: 80.0%

4-Phenyl-1,2,4-triazolidine-3,5-dione (4233-33-4) + 5-oxo-Na-14,21-dehydrosecodine (88839-91-2) → 2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.02,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester (88839-92-3)

Guidance literature:

In dichloromethane; at 20 ℃; for 0.0833333h;

DOI:10.1016/S0040-4020(01)88613-0

Reference yield:

3-ethylpyridine (536-78-7,151103-56-9) → 2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.02,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester (88839-92-3)

Guidance literature:

Multi-step reaction with 10 steps

1: 99 percent / 72 h / 20 °C

2: NaBH₄ / 1.) abs. ethanol, 0 deg C, 3 h; 2.) 20 deg C, 21 h

3: 83 percent / benzene / 5 h / Heating

4: 93 percent / MeLi, HCl, Et₃N / diethyl ether / 1 h / 0 °C

5: 95 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

6: 97 percent / NaBH₄, NH₄Cl / tetrahydrofuran; methanol / 0.08 h / 20 °C

7: 72 percent / 2,4,6-trimethyl benzoic acid / 3 h / 185 °C / Heating

8: 93 percent / Br₂ / CH₂Cl₂ / 0.08 h / -78 °C

9: 99 percent / ethyl aluminum dichloride / hexane; hexamethylphosphoric acid triamide / 24 h / 20 °C

10: 80 percent / CH₂Cl₂ / 0.08 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; mesitylenecarboxylic acid; methyllithium; bromine; ethylaluminum dichloride; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane; benzene;

DOI:10.1016/S0040-4020(01)88613-0

Reference yield:

indolyl-3-glyoxylyl chloride (22980-09-2) → 2-[3-[2-(11-Ethyl-3,5-dioxo-4-phenyl-2,4,6,8-tetraaza-tricyclo[5.2.2.02,6]undec-10-en-8-yl)-2-oxo-ethyl]-1-(toluene-4-sulfonyl)-1H-indol-2-yl]-acrylic acid methyl ester (88839-92-3)

Guidance literature:

Multi-step reaction with 7 steps

1: 93 percent / MeLi, HCl, Et₃N / diethyl ether / 1 h / 0 °C

2: 95 percent / Et₃N / CH₂Cl₂ / 48 h / 20 °C

3: 97 percent / NaBH₄, NH₄Cl / tetrahydrofuran; methanol / 0.08 h / 20 °C

4: 72 percent / 2,4,6-trimethyl benzoic acid / 3 h / 185 °C / Heating

5: 93 percent / Br₂ / CH₂Cl₂ / 0.08 h / -78 °C

6: 99 percent / ethyl aluminum dichloride / hexane; hexamethylphosphoric acid triamide / 24 h / 20 °C

7: 80 percent / CH₂Cl₂ / 0.08 h / 20 °C

With hydrogenchloride; sodium tetrahydroborate; mesitylenecarboxylic acid; methyllithium; bromine; ethylaluminum dichloride; ammonium chloride; triethylamine; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; diethyl ether; hexane; dichloromethane;

DOI:10.1016/S0040-4020(01)88613-0

upstream raw materials:

4-Phenyl-1,2,4-triazolidine-3,5-dione

5-oxo-N_a-14,21-dehydrosecodine

3-ethylpyridine

indolyl-3-glyoxylyl chloride

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