tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate

Base Information

• Chemical Name: tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate
• CAS No.: 1335137-66-0
• Molecular Formula: C₁₈H₂₃BrN₂O₂
• Molecular Weight: 379.297
• Mol file: 1335137-66-0.mol

Synonyms:tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate

Chemical Property of tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate

There total 2 articles about tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-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:

tert-butyl (2S,4S)-2-ethynyl-4-methyl-pyrrolidine-1-carboxylate (1335137-65-9) + 5-bromo-2-iodo-aniline (64085-52-5) → tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate (1335137-66-0)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 3h; Inert atmosphere;

Reference yield:

4-bromo-1-iodo-2-nitrobenzene (112671-42-8) → tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate (1335137-66-0)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; tin(ll) chloride / ethanol; water / 0.25 h / -10 - 60 °C

2: triethylamine; copper(l) iodide / bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

With hydrogenchloride; copper(l) iodide; triethylamine; tin(ll) chloride; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; ethanol; water;

Reference yield:

tert-butyl (2S,4S)-2-[2-(2-amino-4-bromo-phenyl)ethynyl]-4-methyl-pyrrolidine-1-carboxylate (1335137-66-0) → methyl N-[(1S)-2-methyl-1-[(2S,4S)-4-methyl-2-[5-[4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carbonyl]propyl]carbamate (1335137-50-2)

Guidance literature:

Multi-step reaction with 4 steps

1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 4 h / 20 °C

2: trifluoroacetic acid / dichloromethane / 1 h

3: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 20 °C

4: sodium hydrogencarbonate; 3-(2-dicyclohexylphosphanylphenyl)-2,4-dimethoxy-benzenesulfonic acid / palladium diacetate / isopropyl alcohol; water / 1 h / 100 °C / Inert atmosphere

With 3-(2-dicyclohexylphosphanylphenyl)-2,4-dimethoxy-benzenesulfonic acid; potassium tert-butylate; sodium hydrogencarbonate; N-ethyl-N,N-diisopropylamine; HATU; trifluoroacetic acid; palladium diacetate; In 1-methyl-pyrrolidin-2-one; dichloromethane; water; N,N-dimethyl-formamide; isopropyl alcohol;

upstream raw materials:

4-bromo-1-iodo-2-nitrobenzene

tert-butyl (2S,4S)-2-ethynyl-4-methyl-pyrrolidine-1-carboxylate

5-bromo-2-iodo-aniline

Downstream raw materials:

methyl N-[(1S)-2-methyl-1-[(2S,4S)-4-methyl-2-[5-[4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]phenyl]-1H-imidazol-2-yl]pyrrolidine-1-carbonyl]propyl]carbamate