2-Cyclopropyl-4-(4-fluorophenyl)-3-[(phenylthio)methyl]quinoline

Base Information

• Chemical Name: 2-Cyclopropyl-4-(4-fluorophenyl)-3-[(phenylthio)methyl]quinoline
• CAS No.: 148516-12-5
• Molecular Formula: C₂₅H₂₀FNS
• Molecular Weight: 385.505
• DSSTox Substance ID: DTXSID801170040
• Mol file: 148516-12-5.mol

Synonyms:DTXSID801170040;148516-12-5;2-Cyclopropyl-4-(4-fluorophenyl)-3-[(phenylthio)methyl]quinoline

Chemical Property of 2-Cyclopropyl-4-(4-fluorophenyl)-3-[(phenylthio)methyl]quinoline

Chemical Property:

• XLogP3: 6.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 5
• Exact Mass: 385.13004898
• Heavy Atom Count: 28
• Complexity: 495

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1CC1C2=NC3=CC=CC=C3C(=C2CSC4=CC=CC=C4)C5=CC=C(C=C5)F

Technology Process of 2-Cyclopropyl-4-(4-fluorophenyl)-3-[(phenylthio)methyl]quinoline

There total 2 articles about 2-Cyclopropyl-4-(4-fluorophenyl)-3-[(phenylthio)methyl]quinoline 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:

2-cyclopropyl-4-(4-fluoro-phenyl)-3-quinoline carboxylic acid ethyl ester (148516-11-4) → 2-Cyclopropyl-4-(4-fluoro-phenyl)-3-phenylsulfanylmethyl-quinoline (148516-12-5)

Guidance literature:

Multi-step reaction with 2 steps

1: lithium aluminum hydride / tetrahydrofuran / from 0 deg C to RT

2: tri-n-butylphosphine / pyridine / Ambient temperature

With lithium aluminium tetrahydride; tributylphosphine; In tetrahydrofuran; pyridine;

DOI:10.1016/S0957-4166(00)82337-X

Reference yield:

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline (121660-11-5) + diphenyldisulfane (882-33-7) → 2-Cyclopropyl-4-(4-fluoro-phenyl)-3-phenylsulfanylmethyl-quinoline (148516-12-5)

Guidance literature:

With tributylphosphine; In pyridine; Yield given; Ambient temperature;

DOI:10.1016/S0957-4166(00)82337-X

Reference yield:

2-Cyclopropyl-4-(4-fluoro-phenyl)-3-phenylsulfanylmethyl-quinoline (148516-12-5) → (6S)-6-{(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-5,6-dihydro-2H-pyran-2-one (148516-15-8)

Guidance literature:

Multi-step reaction with 8 steps

1: 1.) tert-butyllithium / 1.) THF, 2.) THF, -78 deg C, 1 h

2: potassium hydroxide / tetrahydrofuran / 3.5 h / Ambient temperature

3: 100 percent / dimethylsulfoxide / 0.5 h / Ambient temperature

4: 67 percent / palladium(II) chloride, copper(II) chloride, NaOAc / 3 h / 760 Torr / Ambient temperature

5: H₂ / Lindlar cat. / methanol / 25 h / Ambient temperature

6: pyridinium p-toluenesulfonate (PPTS) / toluene / 1.5 h / Heating

7: m-chloroperbenzoic acid (m-CPBA) / CH₂Cl₂ / 1.) -78 deg C, 1 h, 2.) -40 deg C, 30 min

8: calcium carbonate / toluene / 0.5 h / Heating

With potassium hydroxide; hydrogen; tert.-butyl lithium; sodium acetate; pyridinium p-toluenesulfonate; 3-chloro-benzenecarboperoxoic acid; calcium carbonate; copper dichloride; palladium dichloride; Lindlar catalyst; In tetrahydrofuran; methanol; dichloromethane; dimethyl sulfoxide; toluene;

DOI:10.1016/S0957-4166(00)82337-X

upstream raw materials:

2-cyclopropyl-4-(4-fluorophenyl)-3-(hydroxymethyl)quinoline

diphenyldisulfane

2-cyclopropyl-4-(4-fluoro-phenyl)-3-quinoline carboxylic acid ethyl ester

Downstream raw materials:

(6S)-6-{(E)-2-[2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl]vinyl}-5,6-dihydro-2H-pyran-2-one

(1R,4S,6R)-4-{(E)-2-[2-Cyclopropyl-4-(4-fluoro-phenyl)-quinolin-3-yl]-vinyl}-3,7-dioxa-bicyclo[4.1.0]heptan-2-one