86847-76-9

Usage

Heterocyclic compound

2-(tert-Butyl)-1H-pyrrolo[3,2-c]pyridine consists of a pyridine ring fused to a pyrrolo ring.

Building block

It is often used in organic synthesis for constructing more complex molecules.

Asymmetrical structure

It possesses an asymmetrical tertiary butyl group, which can influence its chemical reactivity and properties.

Potential applications

It has been studied for its potential use in pharmaceuticals and materials science.

Versatility

tBu-PP is a versatile compound with a wide range of potential applications in the field of organic chemistry.

Upstream product

• 3282-30-2 pivaloyl chloride 
• 113975-41-0 2,2-dimethyl-N-<3-(3,3-dimethyl-2-oxobutyl)-4-pyridinyl>propanamide 
• 86847-73-6 2,2-Dimethyl-N-(3-methyl-4-pyridinyl)propanamide 
• 504-24-5 4-aminopyridine 
• 113975-33-0 2,2-dimethyl-N-(3-iodo-4-pyridinyl)propanamide 
• 70298-89-4 4-N-pivaloylaminopyridine 

Relevant academic research and scientific papers

Metalation/SRN1 Coupling in Heterocyclic Synthesis. A Convenient Methodology for Ring Functionalization

Lithiation, iodination, and fluorine substitution on 2-fluoropyridine gave 2-substituted 3-iodopyridines, which were further subjected to iodine SRN1 substitution by carbon, sulfur, and phosphorus nucleophiles.Iodine substitution by enolates on 2-amino-3-iodopyridines afforded ketones, which were further cyclized to various 1,2-disubstituted pyrrolopyridines. 2-Amino-3-iodo-, 3-amino-4-iodo, and 4-amino-3-iodopyridines were prepared by directed metalation of 2-, 3-, and 4-(pivaloylamino)pyridines.Substitution of iodine by enolates under SRN1 conditions and acidic cyclization led to various 2-substituted pyrrolo, --, and -pyridines in high yields.

Regiospecific Electrophilic Substitution of Aminopyridines: Ortho Lithiation of 2-, 3-, and 4-(Pivaloylamino)pyridines

2- and 4-(pivaloylamino)pyridines have been shown to undergo metalation exclusively at C-3 and these smoothly react with a variety of electrophiles to produce 2,3- and 3,4-disubstituted pyridines, respectively.Removal of the pivaloyl protecting group results in overall electrophilic substitution of an aminopyridine.Utilization of this method is exemplified by efficient syntheses of 2- and 4-aminonicotinaldehydes.Minor modifications of the reaction conditions permitted exclusive ortho metalation of 2-(pivaloylamino)pyridines additionally functionalized by chloro, fluoro, or methyl groups.Although the major product from reaction of 3-(pivaloylamino)pyridine by this method was metalation at C-4, the reaction was complicated by substantial quantities of product derived from nucleophilic attack by n-butyllithium on the pyridine nucleus.