ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate

Base Information

Chemical Name:ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate
CAS No.:794547-74-3
Molecular Formula:C₂₈H₃₀N₂O₅
Molecular Weight:474.557
Hs Code.:

Synonyms:ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate

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Chemical Property of ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate

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Technology Process of ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate

There total 1 articles about ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-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: 47.0%

: 5162-44-7
1-bromo-4-butene

: 794547-72-1
ethyl 5-hydroxy-2-(4-methoxybenzyl)-10-methyl-1-oxo-1,2,3,10-tetrahydroazepino[3,4-b]indole-4-carboxylate

: 794547-74-3
ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate

Guidance literature:: With potassium carbonate; In acetone; for 72h; Heating;
DOI:10.1016/j.tet.2004.07.069

Reference yield: 99.0%

: 794547-74-3
ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate

: 794547-78-7
4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-3,4-dihydroazepino[3,4-b]indole-1,5(2H,10H)-1,5-dione

Guidance literature:: With lithium hydroxide; In ethanol; water; for 0.5h; Heating;
DOI:10.1016/j.tet.2004.07.069

Reference yield:

: 794547-74-3
ethyl 4-(3-butenyl)-2-(4-methoxybenzyl)-10-methyl-1,5-dioxo-1,2,3,4,5,10-hexahydroazepino[3,4-b]indole-4-carboxylate

: C₂₅H₂₄N₂O₃CH₂

Guidance literature:: Multi-step reaction with 5 steps

1: 99 percent / LiOH*H₂O / ethanol; H₂O / 0.5 h / Heating

2: LiHMDS; Br₂ / tetrahydrofuran / 0.17 h / -78 °C

3: DBU / dimethylformamide / 2 h / 20 °C

4: 56 percent / TiCl₄ / CH₂Cl₂ / 15 h / -40 - 20 °C

5: 93 percent / [bis(tricyclohexylphosphine)benzylideneruthenium(IV)]Cl₂ / CH₂Cl₂ / 12 h / 20 °C

With Grubbs catalyst first generation; lithium hydroxide; bromine; titanium tetrachloride; 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium hexamethyldisilazane; In tetrahydrofuran; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4: Sakurai allylation;
DOI:10.1016/j.tet.2004.07.069