2-(4-Fluorophenyl)-1H-indole-3-ethanamine

Base Information

• Chemical Name: 2-(4-Fluorophenyl)-1H-indole-3-ethanamine
• CAS No.: 736948-99-5
• Molecular Formula: C₁₆H₁₅FN₂
• Molecular Weight: 254.307
• DSSTox Substance ID: DTXSID901273346
• Mol file: 736948-99-5.mol

Synonyms:DTXSID901273346;2-(4-Fluorophenyl)-1H-indole-3-ethanamine;SR-01000049687;SR-01000049687-1;736948-99-5

Chemical Property of 2-(4-Fluorophenyl)-1H-indole-3-ethanamine

Chemical Property:

• XLogP3: 3.1
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 3
• Exact Mass: 254.12192665
• Heavy Atom Count: 19
• Complexity: 289

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1=CC=C2C(=C1)C(=C(N2)C3=CC=C(C=C3)F)CCN

Technology Process of 2-(4-Fluorophenyl)-1H-indole-3-ethanamine

There total 5 articles about 2-(4-Fluorophenyl)-1H-indole-3-ethanamine 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: 71.0%

tryptamine (61-54-1) + 4-fluoro-1-iodobenzene (352-34-1) → 2-[2-(4-fluoro-phenyl)-1H-indol-3-yl]-ethylamine (736948-99-5)

Guidance literature:

With palladium diacetate; potassium carbonate; at 100 ℃; for 20h; regioselective reaction; Sealed tube;

DOI:10.1021/acs.orglett.0c03668

Reference yield:

2-{2-[2-(4-Fluoro-phenyl)-1H-indol-3-yl]-ethyl}-isoindole-1,3-dione (192182-24-4) → 2-[2-(4-fluoro-phenyl)-1H-indol-3-yl]-ethylamine (736948-99-5)

Guidance literature:

With hydrazine; In tetrahydrofuran; ethanol; water;

DOI:10.1016/S0960-894X(00)00707-1

Reference yield:

tryptamine (61-54-1) → 2-[2-(4-fluoro-phenyl)-1H-indol-3-yl]-ethylamine (736948-99-5)

Guidance literature:

Multi-step reaction with 4 steps

1: tetrahydrofuran / Heating

2: pyridine hydrobromide perbromide / tetrahydrofuran; CHCl₃

3: Pd(PPh₃)4; Na₂CO₃; LiCl / toluene; ethanol / Heating

4: hydrazine / H₂O; tetrahydrofuran; ethanol

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; pyridinium hydrobromide perbromide; sodium carbonate; lithium chloride; hydrazine; In tetrahydrofuran; ethanol; chloroform; water; toluene; 3: Suzuki coupling;

DOI:10.1016/S0960-894X(00)00707-1

upstream raw materials:

2-{2-[2-(4-Fluoro-phenyl)-1H-indol-3-yl]-ethyl}-isoindole-1,3-dione

tryptamine

N-phthalimidotryptamine

2-(2-(2-bromo-1H-indol-3-yl)ethyl)isoindoline-1,3-dione