132833-51-3

Usage

Uses

Used in Pharmaceutical Industry:
4-(4-Bromobenzyl)morpholine is used as a building block for the synthesis of pharmaceuticals due to its potential biological activities and its role in creating various medicinal compounds. It contributes to the development of drugs for the treatment of a range of diseases, enhancing the therapeutic options available.
Used in Organic Synthesis:
In the field of organic synthesis, 4-(4-Bromobenzyl)morpholine is used as an intermediate for creating fine chemicals. Its unique structure allows it to participate in various chemical reactions, facilitating the production of complex organic molecules.
Used as a Reagent in Organic Reactions:
4-(4-Bromobenzyl)morpholine also serves as a reagent in organic reactions, where its bromo group and morpholine structure can be leveraged to drive specific chemical transformations, contributing to the advancement of synthetic methodologies.
Used in the Synthesis of Complex Molecules:
As a starting material, 4-(4-Bromobenzyl)morpholine is instrumental in the synthesis of complex molecules, which may have applications in various fields such as materials science, agrochemicals, and specialty chemicals. Its ability to be incorporated into intricate molecular structures underscores its importance in chemical research and development.

InChI:InChI=1/C11H14BrNO/c12-11-3-1-10(2-4-11)9-13-5-7-14-8-6-13/h1-4H,5-9H2

Upstream product

• 110-91-8 morpholine 
• 1122-91-4 4-bromo-benzaldehyde 
• 55883-45-9 4-bromobenzyliodide 
• 1233656-28-4 C₁₆H₁₈BrO₄P 
• 459-49-4 p-bromobenzyl fluoride 
• 589-15-1 1-bromomethyl-4-bromobenzene 
• 873-75-6 4-bromobenzenemethanol 
• 106-38-7 para-bromotoluene 
• 75382-07-9 (4-bromophenyl)-1-morpholinoacetonitrile 

Downstream Products

• 364794-79-6 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzyl]morpholine 
• 945537-27-9 C₂₁H₂₂N₂O 
• 1093191-20-8 4-[4-(2-(trimethylsilyl)ethynyl)benzyl]morpholine 
• 933986-59-5 4-(morpholinomethyl)phenylacetylene 
• 1395409-50-3 methyl (2S,3R,4S,5S)-3,4-dihydroxy-5-(4-{2-[4-(morpholinomethyl)phenyl]ethynyl}phenyl)-2,3,4,5-tetrahydrofuran-2-carboxylate 
• 1395409-38-7 (2S,3R,4S,5S)-N,3,4-trihydroxy-5-(4-(2-(4-(morpholinomethyl)phenyl)ethynyl)phenyl)-tetrahydrofuran-2-carboxamide 
• 1373010-57-1 (1S,2R)-5'-methoxy-2-(3-((E)-4-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one hydrochloride 
• 1338799-79-3 (1R,2S)-(E)-5'-methyl-2-(3-(4-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one 2,2,2-trifluoroacetate 
• 1338806-35-1 (1R,2S)-(E)-5'-methoxy-1'-methyl-2-(3-(4-(morpholinomethyl)styryl)-1H-indazol-6-yl)spiro[cyclopropane-1,3'-indolin]-2'-one hydrochloride 

Relevant academic research and scientific papers

Design and synthesis of benzopyran-based inhibitors of the hypoxia-inducible factor-1 pathway with improved water solubility

While progress has been made in treating cancer, cytotoxic chemotherapeutic agents are still the most widely used drugs and are associated with severe side-effects. Drugs that target unique molecular signalling pathways are needed for treating cancer with low or no intrinsic toxicity to normal cells. Our goal is to target hypoxic tumours and specifically the hypoxia inducible factor (HIF) pathway for the development of new cancer therapies. To this end, we have previously developed benzopyran-based HIF-1 inhibitors such as arylsulfonamide KCN1. However, KCN1 and its earlier analogs have poor water solubility, which hamper their applications. Herein, we describe a series of KCN1 analogs that incorporate a morpholine moiety at various positions. We found that replacing the benzopyran group of KCN1 with a phenyl group with a morpholinomethyl moiety at the para positions had minimal effect on potency and improved the water solubility of two new compounds by more than 10-fold compared to KCN1, the lead compound.

Shuttle arylation by Rh(I) catalyzed reversible carbon–carbon bond activation of unstrained alcohols

The advent of transfer hydrogenation and borrowing hydrogen reactions paved the way to manipulate simple alcohols in previously unthinkable manners and circumvented the need for hydrogen gas. Analogously, transfer hydrocarbylation could greatly increase the versatility of tertiary alcohols. However, this reaction remains unexplored because of the challenges associated with the catalytic cleavage of unactivated C–C bonds. Herein, we report a rhodium(I)-catalyzed shuttle arylation cleaving the C(sp2)–C(sp3) bond in unstrained triaryl alcohols via a redox-neutral β-carbon elimination mechanism. A selective transfer hydrocarbylation of substituted (hetero)aryl groups from tertiary alcohols to ketones was realized, employing benign alcohols as latent C-nucleophiles. All preliminary mechanistic experiments support a reversible β-carbon elimination/migratory insertion mechanism. In a broader context, this novel reactivity offers a new platform for the manipulation of tertiary alcohols in catalysis.

Thiourea-Catalyzed C?F Bond Activation: Amination of Benzylic Fluorides

We describe the first thiourea-catalyzed C?F bond activation. The use of a thiourea catalyst and Ti(OiPr)4 as a fluoride scavenger allows the amination of benzylic fluorides to proceed in moderate to excellent yields. Preliminary results with S- and O-based nucleophiles are also presented. DFT calculations reveal the importance of hydrogen bonds between the catalyst and the fluorine atom of the substrate to lower the activation energy during the transition state.

1,5,7-TRISUBSTITUTED ISOQUINOLINE DERIVATIVES, PREPARATION THEREOF, AND USE THEREOF IN MEDICINES

The present disclosure relates to 1,5,7-trisubstituted isoquinoline derivatives, their preparation and pharmaceutical use. In particular, the present disclosure discloses a compound of formula (I) or a pharmaceutically acceptable salt, stereoisomer, solvate or prodrug thereof, and a preparation method and use thereof. The definitions of the groups in the formula can be found in the specification and claims.

Photochemical benzylic bromination in continuous flow using BrCCl3 and its application to telescoped p-methoxybenzyl protection

BrCCl3 represents a rarely used benzylic brominating reagent with complementary reactivity to other reagents. Its reactivity has been revisited in continuous flow, revealing compatibility with electron-rich aromatic substrates. This has brought about the development of a p-methoxybenzyl bromide generator for PMB protection, which was successfully demonstrated on a pharmaceutically relevant intermediate on 11 g scale, giving 91% yield and a PMB-Br space-time-yield of 1.27 kg L?1 h?1

Mitsunobu Reaction Using Basic Amines as Pronucleophiles

A novel protocol for extending the scope of the Mitsunobu reaction to include amine nucleophiles to form C-N bonds through the utilization of N-heterocyclic phosphine-butane (NHP-butane) has been developed. Both aliphatic alcohols and benzyl alcohols are suitable substrates for C-N bond construction. Various acidic nucleophiles such as benzoic acids, phenols, thiophenol, and secondary sulfonamide also provide the desired products of esters, ethers, thioether, and tertiary sulfonamide with 43-93% yields. Importantly, C-N bond-containing pharmaceuticals, Piribedil and Cinnarizine, have been synthesized in one step from the commercial amines under this Mitsunobu reaction system.

Structure-based optimization leads to the discovery of NSC765844, a highly potent, less toxic and orally efficacious dual PI3K/mTOR inhibitor

The phosphoinositide 3-kinase (PI3K) family is one of the most frequently activated enzymes in a wide range of human cancers; thus, inhibition of PI3K represents a promising strategy for cancer therapy. Herein, a series of benzylamine substituted arylsulfonamides were designed and synthesized as dual PI3K/mTOR inhibitors using a strategy integrating focused library design and virtual screening, resulting in the discovery of 13b (NSC765844). The compound 13b exhibits highly potent enzyme inhibition with IC50s of 1.3, 1.8, 1.5, 3.8 and 3.8?nM for PI3Kα, β, γ, δ, and mTOR, respectively. 13b was further evaluated in NCI by an in?vitro cytotoxic screening program. Broad-spectrum antitumor activities with mean GI50value of 18.6?nM against approximately 60 human tumor cell lines were found. 13b displayed favorable physicochemical properties and superior pharmacokinetic profiles for animal studies. It significantly inhibited tumor growth when administered orally in an A549 non-small-cell lung carcinoma xenograft and BEL7404 human hepatocellular carcinoma xenograft models. On the basis of its excellent in?vivo efficacy and superior pharmacokinetic profiles, 13b has been selected for further preclinical investigation as a promising anticancer drug candidate.

AUTOTAXIN INHIBITORS

The present invention relates to compounds of formula (I): wherein R1, R2, R3, R4a, R4b, R4C, R4d, L, A, Q, W and HET are each as defined herein. The compounds of the present inv

Anti-Malarial Agents

The present invention relates to a novel class of quinolone-4-carboxamide Pf3D7 inhibitors of general formula (I) (Formula (I)) wherein R1, R2, R3, R4, R5, R6, R7, R8 and X are as defined herein, to their use in medicine, and in the treatment of malaria in particular, to compositions containing them, to processes for their preparation and to intermediates used in such processes.

Enabling nucleophilic substitution reactions of activated alkyl fluorides through hydrogen bonding

It was discovered that the presence of water as a cosolvent enables the reaction of activated alkyl fluorides for bimolecular nucleophilic substitution reactions. DFT calculations show that activation proceeds through stabilization of the transition structure by a stronger F···H 2O interaction and diminishing C-F bond elongation, and not simple transition state electrostatic stabilization. Overall, the findings put forward a distinct strategy for C-F bond activation through H-bonding.