5-(4-Chlorophenyl)furan-2-carboxamide

Base Information

• Chemical Name: 5-(4-Chlorophenyl)furan-2-carboxamide
• CAS No.: 57753-81-8
• Molecular Formula: C11H8ClNO2
• Molecular Weight: 221.64000
• DSSTox Substance ID: DTXSID70406535
• Wikidata: Q82211542
• Mol file: 57753-81-8.mol

Synonyms:5-(4-chlorophenyl)furan-2-carboxamide;57753-81-8;2-Furancarboxamide, 5-(4-chlorophenyl)-;SCHEMBL7118702;5-(p-Chlorophenyl)-2-furamide;SCHEMBL11624844;5-(4-chlorophenyl)-2-furamide;DTXSID70406535;XTPWJBLYVBMEQX-UHFFFAOYSA-N;AKOS000299323;BB 0244290;CS-0453888;AP-970/05452051;EN300-25422233;5-(4-Chloro-phenyl)-furan-2-carboxylic acid amide;Z84563514

Chemical Property of 5-(4-Chlorophenyl)furan-2-carboxamide

Chemical Property:

• PSA: 56.23000
• LogP: 3.39920
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 221.0243562
• Heavy Atom Count: 15
• Complexity: 239

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C2=CC=C(O2)C(=O)N)Cl

Technology Process of 5-(4-Chlorophenyl)furan-2-carboxamide

There total 4 articles about 5-(4-Chlorophenyl)furan-2-carboxamide 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: 79.0%

5-bromo-furan-2-carboxylic acid amide (6134-61-8) + 4-Chlorophenylboronic acid (1679-18-1) → 5-(4-chlorophenyl)furan-2-carboxamide (57753-81-8)

Guidance literature:

With dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); TPGS-750-M; triethylamine; In water; at 50 ℃; Inert atmosphere;

DOI:10.1039/c4gc00853g

Reference yield:

5-bromo-furan-2-carboxylic acid (585-70-6) → 5-(4-chlorophenyl)furan-2-carboxamide (57753-81-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N-hydroxybenzotriazole ammonium salt; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 2 h / 20 °C

2: TPGS-750-M; triethylamine; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II) / water / 50 °C / Inert atmosphere

With N-hydroxybenzotriazole ammonium salt; dichloro[1,1'-bis(di-t-butylphosphino)ferrocene]palladium(II); TPGS-750-M; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In water; N,N-dimethyl-formamide; 2: |Suzuki-Miyaura Coupling;

DOI:10.1039/c4gc00853g

Reference yield:

2-furanoic acid (88-14-2) → 5-(4-chlorophenyl)furan-2-carboxamide (57753-81-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: acetic acid; bromine / 16 h / 100 °C

2.1: potassium fluoride; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) / 1,4-dioxane; water / 16 h / 100 °C / Sealed tube

3.1: 1,1'-carbonyldiimidazole / N,N-dimethyl-formamide / 1 h / 20 °C / Inert atmosphere

3.2: 0 - 20 °C / Inert atmosphere

With potassium fluoride; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); bromine; acetic acid; 1,1'-carbonyldiimidazole; In 1,4-dioxane; water; N,N-dimethyl-formamide; 2.1: |Suzuki Coupling;

DOI:10.1016/j.bioorg.2020.104586

upstream raw materials:

5-bromo-furan-2-carboxylic acid

5-bromo-furan-2-carboxylic acid amide

4-Chlorophenylboronic acid

2-furanoic acid

Downstream raw materials:

[3H]-A-803467

Refernces

• 1、 Wagner, Patrick,Bollenbach, Maud,Doebelin, Christelle,Bihel, Frederic,Bourguignon, Jean-Jacques,Salome, Christophe,Schmitt, Martine. "T-BuXPhos: A highly efficient ligand for Buchwald-Hartwig coupling in water". . p. 4170 - 4178. Retrieved 2014/09/29.