42770-14-9

Usage

InChI:InChI=1/C9H14N2/c1-2-3-5-8-6-4-7-11-9(8)10/h4,6-7H,2-3,5H2,1H3,(H2,10,11)

Upstream product

• 1260537-79-8 Tert-butyl 3-butylpyridin-2-ylcarbamate 
• 38427-94-0 N-(tert-butoxycarbonyl)-2-aminopyridine 
• 504-29-0 2-aminopyridine 
• 539-32-2 3-butylpyridine 
• 108-99-6 3-Methylpyridine 

Relevant academic research and scientific papers

Rational Development of Remote C?H Functionalization of Biphenyl: Experimental and Computational Studies

A simple and efficient nitrile-directed meta-C?H olefination, acetoxylation, and iodination of biaryl compounds is reported. Compared to the previous approach of installing a complex U-shaped template to achieve a molecular U-turn and assemble the large-sized cyclophane transition state for the remote C?H activation, a synthetically useful phenyl nitrile functional group could also direct remote meta-C?H activation. This reaction provides a useful method for the modification of biaryl compounds because the nitrile group can be readily converted to amines, acids, amides, or other heterocycles. Notably, the remote meta-selectivity of biphenylnitriles could not be expected from previous results with a macrocyclophane nitrile template. DFT computational studies show that a ligand-containing Pd–Ag heterodimeric transition state (TS) favors the desired remote meta-selectivity. Control experiments demonstrate the directing effect of the nitrile group and exclude the possibility of non-directed meta-C?H activation. Substituted 2-pyridone ligands were found to be key in assisting the cleavage of the meta-C?H bond in the concerted metalation–deprotonation (CMD) process.

Process for producing azasulfonium salts and rearrangement thereof to thio-ethers

Preparing ortho-substituted anilines by reacting an N-chloroaniline with a non-carbonylic di-hydrocarbon sulfide to form an azasulfonium chloride, reacting the azasulfonium chloride with a strong base to form an aniline substituted in the 2-position with a hydrocarbon-S-hydrocarbyl thio-ether group. The ortho-substituted thio-ether compounds can be reduced with a de-sulfurizing reducing agent such as Raney nickel or the like to form the ortho-alkylated aniline. The aniline may be an amino-pyridine. The azasulfonium salt and thio-ether intermediate products can be isolated and recovered. If desired, the thio-ether compounds can be reduced to form ortho-alkylated aniline products which are useful as intermediates for a wide variety of purposes, including their uses in making dyes, herbicides, and the like.