tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

Base Information

Chemical Name:tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate
CAS No.:1574306-31-2
Molecular Formula:C₂₄H₂₅N₅O₃
Molecular Weight:431.494
Hs Code.:

Synonyms:tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

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Chemical Property of tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

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Technology Process of tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

There total 6 articles about tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-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: 80.0%

Indole-2-carboxylic acid: 1477-50-5,1228050-17-6
Indole-2-carboxylic acid

: 1574306-50-5
tert-butyl 4-(3-aminophenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

: 1574306-31-2
tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

Guidance literature:: Indole-2-carboxylic acid; With 4-methyl-morpholine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; In dichloromethane; at 20 ℃; for 0.5h;

tert-butyl 4-(3-aminophenyl)-2-(methylamino)-1H-imidazole-1-carboxylate; In dichloromethane; at 35 ℃; for 24h;
DOI:10.1016/j.ejmech.2013.12.034

Reference yield:

: 2227-64-7
3'-nitro-2-bromoacetophenone

: 1574306-31-2
tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

Guidance literature:: Multi-step reaction with 5 steps

1.1: dmap / acetonitrile / 15 h / 50 °C

2.1: hydrazine hydrate / ethanol / 0.67 h / 120 °C / Microwave irradiation

3.1: sodium hydroxide / methanol; water / pH 9

3.2: 3 h / 20 °C

4.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 5 h / 20 °C

5.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / dichloromethane / 0.5 h / 20 °C

5.2: 24 h / 35 °C

With 4-methyl-morpholine; dmap; palladium on activated charcoal; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; hydrazine hydrate; sodium hydroxide; In tetrahydrofuran; methanol; ethanol; dichloromethane; water; acetonitrile;
DOI:10.1016/j.ejmech.2013.12.034

Reference yield:

: 1574306-48-1
2-(methylamino)-4-(3-nitrophenyl)-1H-imidazolium bromide

: 1574306-31-2
tert-butyl 4-(3-(1H-indole-2-carboxamido)phenyl)-2-(methylamino)-1H-imidazole-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: sodium hydroxide / methanol; water / pH 9

1.2: 3 h / 20 °C

2.1: palladium on activated charcoal; hydrogen / tetrahydrofuran / 5 h / 20 °C

3.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; 4-methyl-morpholine / dichloromethane / 0.5 h / 20 °C

3.2: 24 h / 35 °C

With 4-methyl-morpholine; palladium on activated charcoal; hydrogen; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; sodium hydroxide; In tetrahydrofuran; methanol; dichloromethane; water;
DOI:10.1016/j.ejmech.2013.12.034