1616667-09-4

Basic information

• Product Name: C₂₀H₁₉ClFN₃O₂
• CAS NO: 1616667-09-4
• Molecular Weight: 387.841
• Mol File: 1616667-09-4.mol

Chemical Properties

• CAS DataBase Reference: C₂₀H₁₉ClFN₃O₂(CAS DataBase Reference)
• NIST Chemistry Reference: C₂₀H₁₉ClFN₃O₂(1616667-09-4)
• EPA Substance Registry System: C₂₀H₁₉ClFN₃O₂(1616667-09-4)

Safety Data

• Hazardous Substances Data: 1616667-09-4(Hazardous Substances Data)

Upstream product

• 1616666-81-9 tert-butyl benzyl(6-chloroquinoxalin-2-yl)carbamate 
• 100-46-9 benzylamine 
• 18671-97-1 2,6-dichloroquinoxaline 
• 1257089-73-8 N-benzyl-N-(6-chloroquinoxalin-2-yl)amine 

Downstream Products

• 1616667-13-0 tert-butyl benzyl(6-chloro-3-(3,5-dimethyl-1H-pyrazol-1-yl)quinoxalin-2-yl)carbamate 
• 1616667-12-9 tert-butyl benzyl(6-chloro-3-(1H-imidazol-1-yl)quinoxalin-2-yl)carbamate 
• 1616667-10-7 tert-butyl benzyl(3-butoxy-6-chloroquinoxalin-2-yl)carbamate 

Relevant articles and documents

C-H FLUORINATION OF HETEROCYCLES WITH SILVER (II) FLUORIDE

The present invention provides compositions and methods for the selective C-H fluorination of nitrogen-containing heteroarenes with AgF2, which has previously been considered too reactive for practical, selective C-H fluorination. Fluorinated heteroarenes are prevalent in numerous pharmaceuticals, agrochemicals and materials. However, the reactions used to introduce fluorine into these molecules require pre-functionalized substrates or the use of F2 gas. The present invention provides a mild and general method for the C-H fluorination of nitrogen-containing heteroarene compounds to 2-fluoro-heteroarenes with commercially available AgF2. In various embodiments, these reactions occur at ambient temperature within one hour and occur with exclusive selectivity for fluorination at the 2-position. Exemplary reaction conditions are effective for fluorinating diazine heteroarenes to form a single fluorinated isomer.

Synthesis and late-stage functionalization of complex molecules through C-H fluorination and nucleophilic aromatic substitution

We report the late-stage functionalization of multisubstituted pyridines and diazines at the position α to nitrogen. By this process, a series of functional groups and substituents bound to the ring through nitrogen, oxygen, sulfur, or carbon are installed. This functionalization is accomplished by a combination of fluorination and nucleophilic aromatic substitution of the installed fluoride. A diverse array of functionalities can be installed because of the mild reaction conditions revealed for nucleophilic aromatic substitutions (SNAr) of the 2-fluoroheteroarenes. An evaluation of the rates for substitution versus the rates for competitive processes provides a framework for planning this functionalization sequence. This process is illustrated by the modification of a series of medicinally important compounds, as well as the increase in efficiency of synthesis of several existing pharmaceuticals.