1501904-97-7

Basic information

• Product Name: C₁₈H₁₅Cl₂F₃N₂O₃
• CAS NO: 1501904-97-7
• Molecular Weight: 435.23
• Mol File: 1501904-97-7.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: C₁₈H₁₅Cl₂F₃N₂O₃(CAS DataBase Reference)
• NIST Chemistry Reference: C₁₈H₁₅Cl₂F₃N₂O₃(1501904-97-7)
• EPA Substance Registry System: C₁₈H₁₅Cl₂F₃N₂O₃(1501904-97-7)

Safety Data

• Hazardous Substances Data: 1501904-97-7(Hazardous Substances Data)

Upstream product

• 1616666-83-1 N-(3,5-dichloropyrid-4-yl)-N-methyl-3-cyclopropylmethoxy-4-difluoromethoxybenzamide 

Downstream Products

• 1616667-27-6 N-methyl-2-octylaminoroflumilast 
• 1616667-26-5 N-methyl-2-isopropoxyroflumilast 

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.

Selective C-H fluorination of pyridines and diazines inspired by a classic amination reaction

Fluorinated heterocycles are prevalent in pharmaceuticals, agrochemicals, and materials. However, reactions that incorporate fluorine into heteroarenes are limited in scope and can be hazardous. We present a broadly applicable and safe method for the site-selective fluorination of a single carbon-hydrogen bond in pyridines and diazines using commercially available silver(II) fluoride. The reactions occur at ambient temperature within 1 hour with exclusive selectivity for fluorination adjacent to nitrogen. The mild conditions allow access to fluorinated derivatives of medicinally important compounds, as well as a range of 2-substituted pyridines prepared by subsequent nucleophilic displacement of fluoride. Mechanistic studies demonstrate that the pathway of a classic pyridine amination can be adapted for selective fluorination of a broad range of nitrogen heterocycles.