25216-70-0

Usage

Uses

Used in Pharmaceutical Industry:
Methyl N-(2-bromophenyl)carbamate is used as a key intermediate in the synthesis of quinazolinyl norepinephrine reuptake inhibitors. These inhibitors are designed to target and modulate the reuptake of norepinephrine, a neurotransmitter involved in the regulation of attention, alertness, and the fight-or-flight response. By inhibiting the reuptake of norepinephrine, these compounds can help alleviate the symptoms of central nervous system disorders, such as attention deficit hyperactivity disorder (ADHD) and other related conditions.
In the development of these quinazolinyl norepinephrine reuptake inhibitors, methyl N-(2-bromophenyl)carbamate plays a crucial role in the formation of the final drug molecule. Its unique structural features allow for the creation of compounds with enhanced selectivity, potency, and pharmacokinetic properties, which are essential for the effective treatment of CNS disorders.
Furthermore, the use of methyl N-(2-bromophenyl)carbamate in the pharmaceutical industry highlights its potential as a versatile building block for the design and synthesis of other therapeutic agents. Its ability to be modified and functionalized allows for the exploration of various chemical pathways, leading to the discovery of novel drugs with improved efficacy and safety profiles.

Upstream product

• 67-56-1 methanol 
• 1592-00-3 2-bromophenyl isocyanate 
• 7154-66-7 2-bromobenzoic acid chloride 
• 88-65-3 2-bromobenzoic-acid 
• 79-22-1 methyl chloroformate 
• 615-36-1 2-bromoaniline 
• 4001-73-4 2-Bromobenzamide 
• 681-84-5 tetramethylorthosilicate 
• 124-38-9 carbon dioxide 

Downstream Products

• 4791-89-3 3,3,3',4'-bis(methylenedioxy)biphenyl 
• 161196-32-3 methyl o-(3',4'-methylenedioxyphenyl)phenylcarbamate 
• 104189-85-7 2-(2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)acetic acid 
• 28643-53-0 1,3-dihydro-1-(phenylmethyl)-2H-benzimidazol-2-one 
• 851012-55-0 4-(2-Fluoro-phenyl)-1H-quinazolin-2-one 
• 5943-92-0 3-cyclohexyl-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 847238-29-3 3-(4-methoxyphenethyl)-2,4-dioxo-1,2,3,4-tetrahydroquinazoline 
• 20865-83-2 1‐benzylquinazoline‐2,4(1H,3H)‐dione 
• 616890-29-0 N-tert-butyl-N′-(methoxycarbonyl)-2-aminobenzamide 
• 615-36-1 2-bromoaniline 

Relevant academic research and scientific papers

Chiral Bifunctional Phosphine-Carboxylate Ligands for Palladium(0)-Catalyzed Enantioselective C?H Arylation

Previous enantioselective Pd0-catalyzed C?H activation reactions proceeding via the concerted metalation-deprotonation mechanism employed either a chiral ancillary ligand, a chiral base, or a bimolecular mixture thereof. This study describes th

Electrochemical Hofmann rearrangement mediated by NaBr: Practical access to bioactive carbamates

An electrochemical Hofmann rearrangement is reported. With the mediation of NaBr, highly corrosive and toxic halogens are avoided. Moreover, this efficient and green approach is well compatible with a broad range of amides, including several commercial medicine derivatives, and provides direct access to synthetically useful carbamates. The synthetic utility of this method is also demonstrated by the preparation of 15N labeling carbamate and gram-scale synthesis of Amantadine.

Synthesis of carbamates from carbon dioxide promoted by organostannanes and alkoxysilanes

A cooperative methoxy transfer between orthosilicate esters and organotin oxides was developed for the synthesis of various N-alkyl and N-aryl carbamates from carbon dioxide in up to 97% isolated yield. The reaction is highly selective and N-alkylated amines are not observed. Density functional theory calculations of the reaction were performed and, together with NMR observations, a plausible mechanism featuring the catalytic regeneration of dialkyltin dialkoxide is proposed.

Synthesis of 5,6-dihydrophenanthridines via N,O-acetal TMS ethers

A concise and high-yielding protocol for the synthesis of 5,6-dihydrophenanthridines is disclosed. The key feature includes a sequential reduction-cyclization reaction of N-acylcarbamates via N,O-acetal TMS ethers as a stable N-acyliminium ion precursor.

Efficient synthesis of methyl carbamate via Hofmann rearrangement in the presence of TsNBr2

An efficient method has been developed for the synthesis of carbamates from the corresponding amides via the Hofmann rearrangement using N,N-dibromo-p-toluenesulfonamide (TsNBr2) in the presence of DBU in methanol. The reaction goes into completion in 10-20 min at 65 °C to produce the corresponding carbamate in excellent yield.

Novel norepinephrine reuptake inhibitors for the treatment of central nervous system disorders

This invention relates to compounds of the formula 1 wherein R1, R2, and R3 and R4 are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.

4-ALKYL-2-HALOANILINE DERIVATIVE AND PROCESS FOR PRODUCING THE SAME

The present invention relates to a compound of formula (1), wherein R1, R2, R3, n, and X are as defined in the specification, and a process for producing the same. This compound is useful as an intermediate for the synthes

A CONVENIENT MODIFICATION OF THE CURTIUS REACTION

A simple one-pot reaction which converts acids into urethanes is described.Acyl chlorides are converted into isocyanates under anhydrous conditions by sodium azide in the presence of a quaternary ammonium salt, followed by alcohol addition to complete the transformation.