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

Base Information

Chemical Name:methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(2-propenyl)amino]-5-iodoquinoline-3-carboxylate
CAS No.:280572-99-8
Molecular Formula:C₂₆H₂₇IN₂O₅
Molecular Weight:574.415
Hs Code.:

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

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

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

There total 10 articles about methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(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%

: 106-95-6
allyl bromide

: 227084-56-2
methyl 8-(benzyloxy)-6-(N-(tert-butyloxycarbonyl)amino)-5-iodoquinoline-3-carboxylate

: 280572-99-8
methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(2-propenyl)amino]-5-iodoquinoline-3-carboxylate

Guidance literature:: With sodium hydride; In N,N-dimethyl-formamide; at 25 ℃; for 2.5h;
DOI:10.1021/jo000177b

Reference yield:

: 24424-99-5
di-tert-butyl dicarbonate

: 280572-99-8
methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(2-propenyl)amino]-5-iodoquinoline-3-carboxylate

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 / 2.5 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

Reference yield:

: 100-39-0
benzyl bromide

: 280572-99-8
methyl 8-(benzyloxy)-6-[N-(tert-butyloxycarbonyl)-N-(2-propenyl)amino]-5-iodoquinoline-3-carboxylate

Guidance literature:: Multi-step reaction with 7 steps

1: 85 percent / NaH; KI / dimethylformamide / 24 h / 25 °C

2: SnCl₂*2H₂O / ethyl acetate / 0.5 h / 70 °C

3: 74 percent / Et₃N / dioxane / 24 h / 70 °C

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

5: 91 percent / methanol / 1.5 h / 4 - 25 °C

6: 88 percent / N-iodosuccinimide; TsOH / tetrahydrofuran; methanol / 46.5 h / 4 - 25 °C

7: 94 percent / NaH / dimethylformamide / 2.5 h / 25 °C

With N-iodo-succinimide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tributyl-amine; sodium hydride; toluene-4-sulfonic acid; triethylamine; potassium iodide; tin(ll) chloride; In tetrahydrofuran; 1,4-dioxane; methanol; ethyl acetate; N,N-dimethyl-formamide; 1: Alkylation / 2: Reduction / 3: Acylation / 4: Carboxylation / 5: Substitution / 6: Iodination / 7: Alkylation;
DOI:10.1021/jo000177b