(2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

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Chemical Name:(2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate
CAS No.:1335317-48-0
Molecular Formula:C₂₁H₂₄BrN₃O₂
Molecular Weight:430.344
Hs Code.:

Synonyms:(2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

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Chemical Property of (2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

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Technology Process of (2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

There total 4 articles about (2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-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: 84.0%

: 766-96-1
4-bromo-1-ethynylbenzene

: 1313207-07-6
(2S,4S)-tert-butyl 2-(5-iodo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

: 1335317-48-0
(2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

Guidance literature:: With copper(l) iodide; triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In N,N-dimethyl-formamide; at 80 ℃; for 16h; Inert atmosphere;

Reference yield:

: 1313207-05-4
(2S,4S)-tert-butyl 2-(4,5-diiodo-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

: 1335317-48-0
(2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 2 steps

1.1: lithium chloride / tetrahydrofuran / 0.17 h / 20 °C

1.2: 0.5 h / -20 °C

1.3: 3 h / -20 - 20 °C

2.1: copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; copper(l) iodide; triethylamine; lithium chloride; In tetrahydrofuran; N,N-dimethyl-formamide; 2.1: |Sonogashira Cross-Coupling;
DOI:10.1021/ml300461f

Reference yield:

: 1313207-03-2
(2S,4S)-tert-butyl 2-(1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

: 1335317-48-0
(2S,4S)-tert-butyl 2-(5-((4-bromophenyl)ethynyl)-1H-imidazol-2-yl)-4-methylpyrrolidine-1-carboxylate

Guidance literature:: Multi-step reaction with 3 steps

1.1: N-iodo-succinimide / dichloromethane / 15 h / 0 - 20 °C

2.1: lithium chloride / tetrahydrofuran / 0.17 h / 20 °C

2.2: 0.5 h / -20 °C

2.3: 3 h / -20 - 20 °C

3.1: copper(l) iodide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; triethylamine / N,N-dimethyl-formamide / 16 h / 80 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-iodo-succinimide; copper(l) iodide; triethylamine; lithium chloride; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3.1: |Sonogashira Cross-Coupling;
DOI:10.1021/ml300461f