1228147-70-3

Upstream product

• 10075-50-0 5-bromo-1H-indole 
• 4595-60-2 2-bromopyrimidine 
• 1722-12-9 2-chloropyrimidine 
• 496-15-1 1-indoline 

Downstream Products

• 1427669-98-4 (5-bromo-1-(pyrimidin-2-yl)-1H-indol-2-yl)(phenyl)methanone 
• 1608124-74-8 5-bromo-2-phenyl-1-(pyrimidin-2-yl)-1H-indole 

Relevant academic research and scientific papers

Cu-mediated direct regioselective C-2 chlorination of indoles

Cu-mediated C-2 chlorination of indoles was accomplished with copper(ii) chloride through the use of a directing pyrimidyl protection group. A highly regioselective manner can be achieved on a range of indole substrates with excellent functional group tolerance.

The copper(ii)-catalyzed and oxidant-promoted regioselective C-2 difluoromethylation of indoles and pyrroles

A novel and efficient approach for the highly selective C-2 difluoromethylation of indole derivatives was developed by using sodium difluoromethylsulfinate (HCF2SO2Na) as the source of difluoromethyl groups and a Cu(ii) complex as the catalyst. Various substrates were well tolerated in this transformation and the desired products were obtained in moderate to good yields. Moreover, the late-stage C-2 difluoromethylation of bioactive molecules containing an indole ring was achieved in good yields. Generally, this reaction features excellent functional group compatibility, broad substrate scope and excellent C-2 selectivity. This journal is

Iridium(III)-Catalyzed Regioselective Carbenoid Insertion C–H Alkylation by α-Diazotized Meldrum's Acid

A practical and straightforward protocol for IrIII-catalyzed regioselective carbenoid insertion C–H alkylation mediated by α-diazotized Meldrum's acid was developed. The assistance of external additives and oxidants was not needed, and the developed IrIIIcatalysis proceeds in a highly efficient manner (e.g., mild reaction conditions, short reaction times and excellent regioselectivity) and demonstrates good compatibility with several privileged substrates, such as valuable N-(2-pyrimidyl)indoles, phenylpyridines, and the marketed drug edaravone and its analogues, and thus provides a good complement to previous methods for the rapid construction of the corresponding alkylated products.

Cu-mediated C2-dehydrogenative homocoupling of indoles via C-H activation assisted by a removable N-pyrimidyl group

A Cu-mediated regioselective, dehydrogenative homocoupling of indoles was developed using AgNO3 as the additive. The easily installed and removed N-pyrimidyl group exerted complete C2 regiocontrol via C-H activation. A series of indole substrates underwent cross-dehydrogenative-homocoupling. This work developed an effective approach for the synthesis of 2,2′-biindole core of a number of chemicals fundamentally important in material and pharmaceutical chemistry.

CF2DSO2Na: An Effective Precursor Reagent for Deuteriodifluoromethylthiolation and Deuteriodifluoromethylation

Deuteriodifluoromethythio (SCF2D) and deuteriodifluoromethyl (CF2D) are important functional groups in pharmaceutical and agrochemical compounds, and the introduction of these functional groups remains a challenging. We herein report a robust reagent for deuteriodifluoromethylthiolation and deuteriodifluoromethylation. Its potentials were successfully showcased by deuteriodifluoromethylation and deuteriodifluoromethylthiolation of indoles with high-level deuterium incorporation. The reagent also has potential for deuteriodifluoromethylation and deuteriodifluoromethylthiolation of wide range of other natural or synthetic bioactive molecules.

Predictable site-selective functionalization: Promoter group assistedpara-halogenation ofN-substituted(hetero)aromatics under metal-free condition

Herein, regioselectivepara-C-H halogenation ofN-pyrimidyl (hetero)aromatics through SEAr (electrophilic aromatic substitution) type reaction is disclosed. SEAr type reaction has been utilized for the C5-bromination of indolines (para-selective) withN-bromosuccinimide under metal and additive-free conditions in good to excellent yields. The developed methodology is also applicable for iodination and challenging chlorination. The pyrimidyl group is identified as a reactivity tuner that also controls the regioselectivity. The present method is also applicable for selective halogenation of aniline, pyridine, indole, oxindole, pyrazole, tetrahydroquinoline, isoquinoline, and carbazole. DFT studies such as Fukui nucleophilicity and natural charge maps also support the observedp-selectivity. Post-functionalization of the title compound into the corresponding arylated, olefinated, and dihalogenated products is achieved in a one-pot, two-step fashion. Late-stage C-H bromination was also executed on drug/natural molecules (harmine, etoricoxib, clonidine, and chlorzoxazone) to demonstrate the applicability of the developed protocol.

N-2-pyrimidyl-3-fluoroindole compound and preparation method and application thereof

The preparation method of the N-2-pyrimidinyl-3-fluoroindole compound shown in the formula (I) comprises the following steps: by taking an acetonitrile solvent as a reaction medium, adding the N-2-pyrimidinyl indole compound shown in the formula (III), se

Access to Branched Allylarenes via Rhodium(III)-Catalyzed C-H Allylation of (Hetero)arenes with 2-Methylidenetrimethylene Carbonate

A rhodium(III)-catalyzed C-H allylation of (hetero)arenes by using 2-methylidenetrimethylene carbonate as an efficient allylic source has been developed for the first time. Five different directing groups including oxime, N-nitroso, purine, pyridine, and pyrimidine were compatible, delivering various branched allylarenes bearing an allylic hydroxyl group in moderate to excellent yields.

Direct Hiyama Cross-Coupling of (Hetero)arylsilanes with C(sp2)-H Bonds Enabled by Cobalt Catalysis

We report a chelation-assisted C-H arylation of various indoles with sterically and electronically diverse (hetero)arylsilanes enabled by cost-effective Cp*-free cobalt catalysis. Key to the success of this strategy is the judicious choice of copper(II) fluoride as a bifunctional sliane activator and catalyst reoxidant. This methodology features a broad substrate scope and good functional group compatibility. The synthetic versatility of this protocol has been highlighted by the gram-scale synthesis and late-stage diversification of biologically active molecules.

Palladium-Catalyzed C-2 and C-3 Dual C-H Functionalization of Indoles: Synthesis of Fluorinated Isocryptolepine Analogues

Here we report a protocol to synthesize diversiform fluorinated isocryptolepine analogues with potential biological activities in one step via directed C-2 and C-3 dual C-H functionalization of indoles. We also attempted to take into account fluorinated imidoyl chlorides as a novel kind of synthons in the directed C-H functionalization reactions. As a result, a variety of fluorinated isocryptolepine analogues were obtained in up to 96% yield. Moreover, we conducted control experiments to disclose the reaction mechanism.