MK -1439 intermediate

Base Information

• Chemical Name: MK -1439 intermediate
• CAS No.: 1155846-86-8
• Molecular Formula: C13H6ClF3N2O2
• Molecular Weight: 314.651
• Mol file: 1155846-86-8.mol

Synonyms:MK -1439 intermediate;Benzonitrile, 3-chloro-5-[[1,2-dihydro-2-oxo-4-(trifluoromethyl)-3-pyridinyl]oxy]-

Chemical Property of MK -1439 intermediate

Chemical Property:

• Boiling Point: 409.4±45.0 °C(Predicted)
• PKA: 10.03±0.10(Predicted)
• PSA: 65.88000
• Density: 1.54±0.1 g/cm3(Predicted)
• LogP: 3.71108

Purity/Quality:

98%,99%, ^*data from raw suppliers

3-Chloro-5-((2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl)oxy)benzonitrile 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: MK -1439 intermediate belongs to heterocyclic derivatives and can be used as pharmaceutical intermediates.

Technology Process of MK -1439 intermediate

There total 24 articles about MK -1439 intermediate 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: 54.1%

3-chloro-5-((2-chloro-4-(trifluoromethyl)pyridin-3-yl)oxy)benzonitrile → 3-chloro-5-((2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl)oxy)benzonitrile (1155846-86-8)

Guidance literature:

With sodium hydroxide; In toluene; at 150 ℃; for 1.75h; Microwave irradiation;

DOI:10.1016/j.bmc.2018.12.039

Reference yield:

(2E/Z,4E)-ethyl 2-(3-chloro-5-cyanophenoxy)-5-ethoxy-3-(trifluoromethyl)penta-2,4-dienoate (1613307-28-0) → 3-chloro-5-((2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl)oxy)benzonitrile (1155846-86-8)

Guidance literature:

With ammonia; In methanol; toluene; at 60 ℃; for 18h;

Reference yield:

zinc(II) cyanide (557-21-1) + 3-(3-bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one (1155846-88-0) → 3-chloro-5-((2-oxo-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl)oxy)benzonitrile (1155846-86-8)

Guidance literature:

1,1'-bis-(diphenylphosphino)ferrocene; palladium diacetate; zinc; In ISOPROPYLAMIDE; at 90 ℃; for 16h; Inert atmosphere;

upstream raw materials:

3-(3-bromo-5-chlorophenoxy)-4-(trifluoromethyl)pyridin-2(1H)-one

copper(I) cyanide

zinc(II) cyanide

3-chloro-5-hydroxybenzonitrile

Downstream raw materials:

tert-butyl 3-{[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]methyl}-1H-pyrazolo[3,4-b]pyridine-1-carboxylate

N-[4-(aminosulfonyl)-2-chlorophenyl]-2-[3-(3-chloro-5-cyanophenoxy)-2-oxo-4-(trifluoromethyl)pyridin-1(2H)-yl]acetamide

3-chloro-5-((2-oxo-1-((5-oxo-4,5-dihydro-1H-1,2,4-triazol-3-yl)methyl)-4-(trifluoromethyl)-1,2-dihydropyridin-3-yl)oxy)benzonitrile

3-{[5-bromo-2-hydroxy-4-(trifluoromethyl)pyridin-3-yl]oxy}-5-chlorobenzonitrile

Refernces

• 1、 Gauthier, Donald R.,Sherry, Benjamin D.,Cao, Yang,Journet, Michel,Humphrey, Guy,Itoh, Tetsuji,Mangion, Ian,Tschaen, David M.. "Highly efficient synthesis of hiv nnrti doravirine". . p. 1353 - 1356. Retrieved 2015.
• 2、 Campeau, Louis-Charles,Chen, Qinghao,Gauvreau, Danny,Girardin, Mélina,Belyk, Kevin,Maligres, Peter,Zhou, Guoyue,Gu, Chaozhan,Zhang, Wei,Tan, Lushi,O'Shea, Paul D.. "A Robust Kilo-Scale Synthesis of Doravirine". . p. 1476 - 1481. Retrieved 2016/08/30.