1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

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Chemical Name:1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide
CAS No.:930304-11-3
Molecular Formula:C₂₇H₂₆Br₂N₄O₂S₂
Molecular Weight:662.469
Hs Code.:

Synonyms:1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

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Chemical Property of 1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

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Technology Process of 1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

There total 10 articles about 1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide 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: 82.0%

: 930304-10-2
(Z)-1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

: 930304-11-3
1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

Guidance literature:: With Lawessons reagent; In toluene; at 100 ℃; for 2h;
DOI:10.1021/ol063038a DOI:10.1016/j.tet.2007.06.089

Reference yield:

: 930304-08-8
1-benzyloxymethylpyrrole-2-carboxylic acid amide

: 930304-11-3
1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

Guidance literature:: Multi-step reaction with 3 steps

1: 94 percent / NBS / tetrahydrofuran / 0.5 h / 20 °C

2: 92 percent / Cs₂CO₃; CuI; N,N'-dimethylethylenediamine / tetrahydrofuran / 17 h / 70 °C

3: 82 percent / Lawesson's reagent / toluene / 2 h / 100 °C

With Lawessons reagent; N-Bromosuccinimide; copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; toluene; 2: Buchwald coupling;
DOI:10.1016/j.tet.2007.06.089

Reference yield:

: 1-benzyloxymethyl-4,5-dibromo-2-methylsulfanyl-1H-imidazole

: 930304-11-3
1-benzyloxymethyl-4,5-dibromopyrrole-2-carbothioic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide

Guidance literature:: Multi-step reaction with 6 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 0.17 h / -78 °C

1.2: tetrahydrofuran; hexane / 0.5 h / -78 °C

2.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C

3.1: 3.79 g / potassium carbonate / methanol / 3 h / 20 °C

4.1: potassium tert-butoxide / tetrahydrofuran / 0.08 h / 20 °C

4.2: 93 percent / tetrahydrofuran / 0.5 h / -78 °C

5.1: 92 percent / Cs₂CO₃; CuI; N,N'-dimethylethylenediamine / tetrahydrofuran / 17 h / 70 °C

6.1: 82 percent / Lawesson's reagent / toluene / 2 h / 100 °C

With Lawessons reagent; copper(l) iodide; n-butyllithium; potassium tert-butylate; potassium carbonate; caesium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; methanol; hexane; toluene; 4.1: Stork-Zhao Wittig reaction / 5.1: Buchwald coupling;
DOI:10.1016/j.tet.2007.06.089