56775-89-4

Upstream product

• 14548-45-9 (4-bromophenyl)-pyridin-3-yl-methanone 
• 205582-30-5 [(dimethylamino)ethyl]triphenylphosphonium bromide 
• 506-59-2 N,N-dimethylammonium chloride 
• 83049-64-3 (E)-3-(4-Bromophenyl)-3-(3-pyridyl)propenal 
• 77470-68-9 (Z)-3-(4-bromophenyl)-3-(3-pyridyl)-2-propenal 
• 41910-98-9 1-(4-bromophenyl)-3-(dimethylamino)-1-(3-pyridyl)propan-1-ol 
• 77744-36-6 (Z)-3-Acetoxy-1-(4-bromophenyl)-1-(3-pyridyl)propene 
• 124-40-3 dimethyl amine 
• 77744-18-4 Acetic acid 1-(4-bromo-phenyl)-1-pyridin-3-yl-allyl ester 
• 82104-42-5 3-(4-bromophenyl)-3-(3-pyridyl)allyl bromide 
• 626-55-1 3-Bromopyridine 
• 2138-34-3 1-(4-bromo-phenyl)-3-dimethylamino-propan-1-one 
• 54950-20-8 methyl nicotinoylacetate 
• 126629-81-0 methyl 3-(4-bromophenyl)-3-oxopropanoate 

Downstream Products

• 82103-83-1 (E)-1-(4-bromophenyl)-3-pthalimido-1-(3-pyridyl)propene 
• 60324-58-5 A 31119 

Relevant academic research and scientific papers

(E)-,(Z)-parallel preparative methods for stereodefined β,β-diaryl- and α,β-diaryl-α,β-unsaturated esters: Application to the stereocomplementary concise synthesis of zimelidine

Parallel and practical methods for the preparation of both (E)- and (Z)-β-aryl1-β-aryl2-α,β-unsaturated esters 1 and (E)- and (Z)-α-aryl1-β-aryl2-α,β-unsaturated esters 2 are described. These methods involve accessible, robust, stereocomplementary N-methylimidazole (NMI)-mediated enol tosylations (14 examples, 70-99 % yield), as well as stereoretentive Suzuki-Miyaura cross-couplings (36 examples, 64-99 % yield). The highlighted feature of the present protocol is the use of parallel and stereocomplementary approaches to obtain highly (E)- and (Z)-pure products 1 and 2 by utilizing sequential enol tosylations and cross-coupling reactions. An expeditious and parallel synthesis of (E)- and (Z)-zimelidine (3), which is a highly representative selective serotonin reuptake inhibitor (SSRI), was performed by utilizing the present methods.

Stereoconservative Reductive Methyl- and Dimethylamination of Isomeric 3,3-Diarylpropenals. Synthetic and Mechanistic Studies on Control of the Stereochemistry

The tertiary allylic amine zimeldine (1Z) and the secondary amine 2Z have been prepared by reductive aminations of (Z)-3-(4-bromophenyl)-3-(3-pyridyl)propenal (3Z) with sodium cyanoborohydride in the presence of dimethylammonium and methylammonium chlorid

Synthesis of 3-Aryl-3-pyridylallylamines Related to Zimelidine via Palladium-Catalyzed Amination

Reaction of aryl pyridyl ketones 1 with vinylmagnesium bromide followed by acetylation of the products 2 with acetic anhydride/Et3N and with 4-(dimethylamino)pyridine (DMAP) as a catalyst gave acetates 3 in high yields.Treatment of acetates 3 with dimethylamine in the presence of a palladium catalyst produced a mixture of E and Z isomers of 3-aryl-3-pyridylallylamines 4.