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

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Chemical Name:(Z)-1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid [2-(1-benzyloxymethyl-2-methylsulfanylimidazol-4-yl)-vinyl]amide
CAS No.:930304-10-2
Molecular Formula:C₂₇H₂₆Br₂N₄O₃S
Molecular Weight:646.402
Hs Code.:

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

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

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

There total 10 articles about (Z)-1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic 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: 92.0%

: 930304-06-6
(Z)-1-benzyloxymethyl-4-(2-iodovinyl)-2-methylsulfanylimidazole

: 930304-09-9
1-benzyloxymethyl-4,5-dibromopyrrole-2-carboxylic acid amide

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

Guidance literature:: With copper(l) iodide; caesium carbonate; N,N`-dimethylethylenediamine; In tetrahydrofuran; at 70 ℃; for 17h;
DOI:10.1021/ol063038a

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 2 steps

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

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

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

Reference yield:

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

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

Guidance literature:: Multi-step reaction with 5 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

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