methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate

Base Information

• Chemical Name: methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate
• CAS No.: 280573-11-7
• Molecular Formula: C₂₆H₂₆ClIN₂O₅
• Molecular Weight: 608.86
• Mol file: 280573-11-7.mol

Synonyms:methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate

Chemical Property of methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate

There total 11 articles about methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-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: 94.0%

methyl 8-(benzyloxy)-6-(N-(tert-butyloxycarbonyl)amino)-5-iodoquinoline-3-carboxylate (227084-56-2) + (E)-1,3-dichloro-prop-1-ene (10061-02-6) → methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate (280573-11-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 12h;

DOI:10.1021/jo000177b

Reference yield: 94.0%

E/Z-1,3-Dichloropropene (542-75-6) + methyl 8-(benzyloxy)-6-(N-(tert-butyloxycarbonyl)amino)-5-iodoquinoline-3-carboxylate (227084-56-2) → methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate (280573-11-7)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃;

DOI:10.1016/S0040-4039(98)00232-9

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) → methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(E-3-chloro-2-propenyl)amino]-5-iodoquinoline-3-carboxylate (280573-11-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 74 percent / Et₃N / dioxane / 24 h / 70 °C

2: 78 percent / Pd(PPh₃)4; n-Bu₃N / 12 h / 100 °C

3: 91 percent / methanol / 1.5 h / 4 - 25 °C

4: 88 percent / N-iodosuccinimide; TsOH / tetrahydrofuran; methanol / 46.5 h / 4 - 25 °C

5: 94 percent / NaH / dimethylformamide / 12 h / 25 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyl-amine; sodium hydride; toluene-4-sulfonic acid; triethylamine; In tetrahydrofuran; 1,4-dioxane; methanol; N,N-dimethyl-formamide; 1: Acylation / 2: Carboxylation / 3: Substitution / 4: Iodination / 5: Alkylation;

DOI:10.1021/jo000177b

upstream raw materials:

E/Z-1,3-Dichloropropene

methyl 8-(benzyloxy)-6-(N-(tert-butyloxycarbonyl)amino)-5-iodoquinoline-3-carboxylate

(E)-1,3-dichloro-prop-1-ene

di-tert-butyl dicarbonate

Downstream raw materials:

methyl 5-(benzyloxy)-3-(tert-butyloxycarbonyl)-1-(chloromethyl)-1,2-dihydro-3H-pyrido[3,2-e]indole-8-carboxylate