tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

Base Information

• Chemical Name: tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate
• CAS No.: 854765-24-5
• Molecular Formula: C₁₈H₁₉F₃N₂O₂
• Molecular Weight: 352.356
• Mol file: 854765-24-5.mol

Synonyms:tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

Chemical Property of tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate

There total 3 articles about tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate 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: 81.0%

tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-4-hydroxypiperidine-1-carboxylate (854765-34-7) → tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate (854765-24-5)

Guidance literature:

With pyridine; trichlorophosphate; at 20 ℃; for 24h;

DOI:10.1248/cpb.53.402

Reference yield:

4-bromo-2-(trifluoromethyl)benzonitrile (191165-13-6) → tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate (854765-24-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

1.2: 32 percent / hexane; tetrahydrofuran / 1 h / 20 °C

2.1: 81 percent / POCl₃; pyridine / 24 h / 20 °C

With pyridine; n-butyllithium; trichlorophosphate; In tetrahydrofuran; hexane;

DOI:10.1248/cpb.53.402

Reference yield:

4-amino-2-trifluoromethylbenzonitrile (654-70-6) → tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-3,6-dihydropyridine-1(2H)-carboxylate (854765-24-5)

Guidance literature:

Multi-step reaction with 3 steps

1.1: HBr; aq. NaNO₂ / 1 h / 5 °C

1.2: 85 percent / CuBr; aq. HBr / 2 h / 20 °C

2.1: n-BuLi / hexane; tetrahydrofuran / 0.25 h / -78 °C

2.2: 32 percent / hexane; tetrahydrofuran / 1 h / 20 °C

3.1: 81 percent / POCl₃; pyridine / 24 h / 20 °C

With pyridine; n-butyllithium; hydrogen bromide; sodium nitrite; trichlorophosphate; In tetrahydrofuran; hexane;

DOI:10.1248/cpb.53.402

upstream raw materials:

tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]-4-hydroxypiperidine-1-carboxylate

4-bromo-2-(trifluoromethyl)benzonitrile

4-amino-2-trifluoromethylbenzonitrile

Downstream raw materials:

4-(1,2,3,6-tetrahydropyridin-4-yl)-2-(trifluoromethyl)benzonitrile

tert-butyl 4-[4-cyano-3-(trifluoromethyl)phenyl]piperidine-1-carboxylate