(4H-Furo[3,2-b]indol-4-yl)(phenyl)methanone

Base Information

• Chemical Name: (4H-Furo[3,2-b]indol-4-yl)(phenyl)methanone
• CAS No.: 66424-75-7
• Molecular Formula: C₁₇H₁₁NO₂
• Molecular Weight: 261.28
• DSSTox Substance ID: DTXSID40497475
• Wikidata: Q82347059
• Mol file: 66424-75-7.mol

Synonyms:(4H-Furo[3,2-b]indol-4-yl)(phenyl)methanone;66424-75-7;DTXSID40497475

Chemical Property of (4H-Furo[3,2-b]indol-4-yl)(phenyl)methanone

Chemical Property:

• XLogP3: 4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 261.078978594
• Heavy Atom Count: 20
• Complexity: 377

Purity/Quality:

85.0-99.8% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)C(=O)N2C3=C(C4=CC=CC=C42)OC=C3

Technology Process of (4H-Furo[3,2-b]indol-4-yl)(phenyl)methanone

There total 6 articles about (4H-Furo[3,2-b]indol-4-yl)(phenyl)methanone 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: 99.0%

N-(2-(3-bromofuran-2-yl)phenyl)benzamide → 4-benzoyl-4H-furo[3,2-b]indole (66424-75-7)

Guidance literature:

With copper(I) thiophene-2-carboxylate; caesium carbonate; N,N`-dimethylethylenediamine; In 1,4-dioxane; for 3h; Reagent/catalyst; Temperature; Catalytic behavior; Reflux; Inert atmosphere;

DOI:10.1021/acs.joc.1c00086

Reference yield:

2-iodophenylamine (615-43-0) → 4-benzoyl-4H-furo[3,2-b]indole (66424-75-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / acetonitrile

2.2: 17 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride; N-Bromosuccinimide / water; ethyl acetate / 20 °C

4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0.17 h / 20 °C

5.1: copper(I) thiophene-2-carboxylate; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 3 h / Reflux; Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; copper(l) iodide; copper(I) thiophene-2-carboxylate; potassium tert-butylate; caesium carbonate; triethylamine; N,N`-dimethylethylenediamine; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; water; ethyl acetate; acetonitrile; 2.1: |Sonogashira Cross-Coupling / 2.2: |Sonogashira Cross-Coupling / 5.1: |Ullmann Condensation;

DOI:10.1021/acs.joc.1c00086

Reference yield:

benzoyl chloride (98-88-4) → 4-benzoyl-4H-furo[3,2-b]indole (66424-75-7)

Guidance literature:

Multi-step reaction with 5 steps

1.1: triethylamine / tetrahydrofuran / 20 °C / Inert atmosphere

2.1: triethylamine; bis-triphenylphosphine-palladium(II) chloride; copper(l) iodide / acetonitrile

2.2: 17 h / 20 °C / Inert atmosphere

3.1: hydrogenchloride; N-Bromosuccinimide / water; ethyl acetate / 20 °C

4.1: potassium tert-butylate / 1-methyl-pyrrolidin-2-one / 0.17 h / 20 °C

5.1: copper(I) thiophene-2-carboxylate; caesium carbonate; N,N`-dimethylethylenediamine / 1,4-dioxane / 3 h / Reflux; Inert atmosphere

With hydrogenchloride; bis-triphenylphosphine-palladium(II) chloride; N-Bromosuccinimide; copper(l) iodide; copper(I) thiophene-2-carboxylate; potassium tert-butylate; caesium carbonate; triethylamine; N,N`-dimethylethylenediamine; In tetrahydrofuran; 1,4-dioxane; 1-methyl-pyrrolidin-2-one; water; ethyl acetate; acetonitrile; 2.1: |Sonogashira Cross-Coupling / 2.2: |Sonogashira Cross-Coupling / 5.1: |Ullmann Condensation;

DOI:10.1021/acs.joc.1c00086

upstream raw materials:

4H-furo[3,2-b]indole

benzoyl chloride

2-iodophenylamine

o-iodobenzanilide

Downstream raw materials:

2,4-dibenzoyl-4H-furo[3,2-b]indole

(4H-furo[3,2-b]indol-2-yl)-phenyl-methanone

4-benzoyl-2-bromo-4H-furo[3,2-b]indole