tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate

Base Information

• Chemical Name: tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate
• CAS No.: 1258934-71-2
• Molecular Formula: C₁₆H₁₅FN₂O₂S
• Molecular Weight: 318.372
• Mol file: 1258934-71-2.mol

Synonyms:tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate

Chemical Property of tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate

There total 4 articles about tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-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: 85.0%

1-ethynyl-4-fluorobenzene (766-98-3) + tert-butyl N-(5-iodo-1,3-thiazol-4-yl)carbamate (1258934-68-7) → tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate (1258934-71-2)

Guidance literature:

With copper(l) iodide; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; caesium carbonate; In tetrahydrofuran; at 50 ℃; for 6h; Inert atmosphere;

DOI:10.1055/s-0030-1258159

Reference yield: 38.0%

1-ethynyl-4-fluorobenzene (766-98-3) + tert-butyl N-(5-iodo-1,3-thiazol-4-yl)carbamate (1258934-68-7) → thiazol-4-ylaminocarboxylic acid tert-butyl ester (1235406-42-4) + tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate (1258934-71-2)

Guidance literature:

With palladium diacetate; sodium carbonate; In N,N-dimethyl-formamide; at 60 ℃; for 20h;

DOI:10.1055/s-0030-1258159

Reference yield:

thiazol-4-ylaminocarboxylic acid tert-butyl ester (1235406-42-4) → tert-butyl N-{5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate (1258934-71-2)

Guidance literature:

Multi-step reaction with 2 steps

1: N-iodo-succinimide / 1,2-dichloro-ethane / 2 h / Reflux

2: caesium carbonate; copper(l) iodide / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / tetrahydrofuran / 6 h / 50 °C / Inert atmosphere

With N-iodo-succinimide; copper(l) iodide; caesium carbonate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; 1,2-dichloro-ethane;

upstream raw materials:

1-ethynyl-4-fluorobenzene

tert-butyl N-(5-iodo-1,3-thiazol-4-yl)carbamate

thiazol-4-ylaminocarboxylic acid tert-butyl ester

Downstream raw materials:

C₁₁H₇FN₂S

5-(4-fluorophenyl)-4H-pyrrolo[2,3-d]thiazole

tert-butyl N-{2-chloro-5-[2-(4-fluorophenyl)ethynyl]-1,3-thiazol-4-yl}carbamate