206193-58-0

Upstream product

• 62-53-3 aniline 
• 133928-61-7 N-phenyl-4-chloro-2-pyridinecarboxamide 
• 24484-93-3 4-Chloro-pyridine-2-carboxylic acid methyl ester 
• 53750-66-6 4-chloro-pyridine-2-carbonyl chloride 
• 107-18-6 allyl alcohol 
• 206193-53-5 4-chloro-3-iodopicolinanilide 

Downstream Products

• 849437-70-3 (+/-)-2,3-dihydro-N-phenyl-3-(2,2,6,6-tetramethylpiperidin-1-yloxymethyl)furo[3,2-c]pyridine-4-carboxamide 
• 849437-78-1 (+/-)-4-benzyloxycarbonyl-2,3-dihydrofuro[3,2-c]pyridine-3-carboxylic acid 
• 849437-76-9 benzyl 4-allyloxy-3-iodopicolinate 
• 849437-77-0 benzyl (+/-)-2,3-dihydro-3-hydroxymethylfuro[3,2-c]pyridine-4-carboxylate 
• 849437-74-7 4-allyloxy-N-t-butyloxycarbonyl-3-iodopicolinanilide 

Relevant academic research and scientific papers

Ortho-directed lithiation studies of 4-chloropicolinanilide : Introduction of functional groups at C-3 and their elaboration to chain extended derivatives via carbon-carbon bond formation

An improved synthesis of 4-chloropicolinanilide (3) is presented. Treatment of 3 with lithium diisopropylamide (LDA) in THF, followed by addition of an electrophile (methyl iodide, iodine, carbon dioxide, trimethylstannyl chloride), gave exclusively the products of C-3 substitution (respectively, the 3-methyl-, 3-iodo, 3-carboxylic acid and 3-trimethylstannyl derivatives of 3). Further treatment of the 3-methyl derivative (7) with carbon dioxide or ethyl bromoacetate produced the one- and two-carbon homologues of 4-chloroquinolinanilide (8 and 9, respectively). The palladium acetate-catalyzed reaction of 4-chloro-3-iodopicolinanilide (10) with various unsaturated derivatives (trimethylsilylacetylene, tri-n-butyl(vinyl)tin, styrene, acrylonitrile, methyl acrylate) afforded the corresponding C-3 cross-coupled products in 70-80% yield. Reaction of 10 with allyl alkoxide, followed by treatment of the product (17) with tri-n-butyltin hydride, provided the 2-methylfuro[3,2-c]pyridine derivative (18) in 85% yield.