2-ETHYNYLPYRROLE-1-CARBOXYLIC ACID, T-BUTYL ESTER

Base Information

• Chemical Name: 2-ETHYNYLPYRROLE-1-CARBOXYLIC ACID, T-BUTYL ESTER
• CAS No.: 467435-75-2
• Molecular Formula: C11H13NO2
• Molecular Weight: 191.22600
• Mol file: 467435-75-2.mol

Synonyms:2-ethynylpyrrole-1-carboxylic acid tert-butyl ester;2-Ethynyl-1H-pyrrole-1-carboxylic Acid 1,1-Dimethylethyl Ester;2-Ethynylpyrrole-1-carboxylic Acid,t-Butyl Ester;

Chemical Property of 2-ETHYNYLPYRROLE-1-CARBOXYLIC ACID, T-BUTYL ESTER

Chemical Property:

• PSA: 31.23000
• LogP: 2.25260
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)

Purity/Quality:

NLT 98% ^*data from raw suppliers

2-Ethynylpyrrole-1-carboxylic Acid, t-Butyl Ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 2-Ethynylpyrrole-1-carboxylic Acid, t-Butyl Ester (cas# 467435-75-2) is a compound useful in organic synthesis.

Technology Process of 2-ETHYNYLPYRROLE-1-CARBOXYLIC ACID, T-BUTYL ESTER

There total 2 articles about 2-ETHYNYLPYRROLE-1-CARBOXYLIC ACID, T-BUTYL ESTER 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%

2-(trimethylsilylethynyl)pyrrole-1-carboxylic acid tert-butyl ester (467435-72-9) → 2-ethynylpyrrole-1-carboxylic acid tert-butyl ester (467435-75-2)

Guidance literature:

With methanol; potassium fluoride; at 20 ℃; for 6h;

DOI:10.1021/ja039237w

Reference yield:

2-bromo-pyrrole-1-carboxylic acid tert-butyl ester (117657-37-1) → 2-ethynylpyrrole-1-carboxylic acid tert-butyl ester (467435-75-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 79 percent / triethylamine; CuI / Pd(PPh₃)2Cl₂ / dioxane / 0.33 h / 80 °C

2: 84 percent / KF; MeOH / 6 h / 20 °C

With methanol; potassium fluoride; copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In 1,4-dioxane; 1: Sonogashira coupling;

DOI:10.1021/ja039237w

Reference yield: 78.0%

2,7-dichloro-1,8-naphthyridine (55243-02-2) + 2-ethynylpyrrole-1-carboxylic acid tert-butyl ester (467435-75-2) → 2,7-bis-(1-tert-butoxycarbonylpyrrol-2-yl)ethynyl-1,8-naphthyridine (467435-77-4)

Guidance literature:

With copper(l) iodide; triethylamine; bis-triphenylphosphine-palladium(II) chloride; In tetrahydrofuran; at 20 ℃; for 40h;

DOI:10.1021/ja039237w

upstream raw materials:

2-(trimethylsilylethynyl)pyrrole-1-carboxylic acid tert-butyl ester

2-bromo-pyrrole-1-carboxylic acid tert-butyl ester

Downstream raw materials:

2,7-bis-(1-tert-butoxycarbonylpyrrol-2-yl)ethynyl-1,8-naphthyridine

Refernces

• 1、 Fang, Jim-Min,Selvi, Srinivasan,Liao, Jen-Hai,Slanina, Zdenek,Chen, Chao-Tsen,Chou, Pi-Tai. "Fluorescent and Circular Dichroic Detection of Monosaccharides by Molecular Sensors: Bis[(Pyrrolyl)ethynyl]naphthyridine and Bis[(Indolyl)ethynyl]naphthyridine". . p. 3559 - 3566. Retrieved 2004.