tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate

Base Information

• Chemical Name: tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate
• CAS No.: 1329167-90-9
• Molecular Formula: C₂₀H₂₄N₄O₄
• Molecular Weight: 384.435
• Mol file: 1329167-90-9.mol

Synonyms:tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate

Chemical Property of tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate

There total 12 articles about tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate 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: 78.0%

2‐(5,5‐dimethyl‐1,3,2‐dioxaborinan‐2‐yl)‐5‐nitroaniline (1329166-69-9) + tert-butyl N-[(1S)-1-(4-chloropyridin-2-yl)but-3-en-1-yl]carbamate (1329171-69-8) → tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate (1329167-90-9)

Guidance literature:

With potassium phosphate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In water; dimethyl sulfoxide; at 90 ℃; for 6h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.9b01768

Reference yield:

di-tert-butyl dicarbonate (24424-99-5) + C15H16N4O2 (1329167-91-0) → tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate (1329167-90-9)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 2h;

Reference yield:

4-chloro-2-pyridinecarbaldehyde (63071-13-6) → tert-butyl N-[(1S)-1-[4-(2-amino-4-nitrophenyl)pyridin-2-yl]but-3-en-1-yl]carbamate (1329167-90-9)

Guidance literature:

Multi-step reaction with 5 steps

1: copper(II) sulfate / dichloromethane / 3 h / 20 °C

2: diethyl ether; tetrahydrofuran / -78 °C

3: potassium phosphate; water / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 5 h / 90 °C

4: hydrogenchloride / 1,4-dioxane; methanol

5: triethylamine / dichloromethane / 2 h / 20 °C

With hydrogenchloride; potassium phosphate; water; copper(II) sulfate; triethylamine; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,4-dioxane; methanol; diethyl ether; dichloromethane; dimethyl sulfoxide;

upstream raw materials:

di-tert-butyl dicarbonate

C₁₅H₁₆N₄O₂

4-chloro-2-pyridinecarbaldehyde

2-bromo 5-nitroaniline

Downstream raw materials:

{(S)-1-[4-(4-nitro-2-pent-4-enoylaminophenyl)pyridin-2-yl]but-3-enyl}carbamic acid tert-butyl ester

C₂₅H₃₂N₄O₃

{4-[2-((S)-1-tert-butoxycarbonylaminobut-3-enyl)pyridin-4-yl]-3-pent-4-enoylaminophenyl}carbamic acid methyl ester

methyl N-(3-(but-3-enoylamino)-4-(2-((1S)-1-((tert-butoxycarbonyl)amino)but-3-en-1-yl)pyridin-4-yl)phenyl)carbamate