87630-40-8

Usage

Synthesis Reference(s)

The Journal of Organic Chemistry, 49, p. 3239, 1984 DOI: 10.1021/jo00191a047Tetrahedron Letters, 24, p. 3455, 1983 DOI: 10.1016/S0040-4039(00)86011-6

InChI:InChI=1/C4H4BrN/c5-4-1-2-6-3-4/h1-3,6H

Upstream product

• 429-41-4 tetrabutyl ammonium fluoride 
• 87630-36-2 3-bromo-1-triisopropylsilanyl-1H-pyrrole 

Downstream Products

• 1403230-02-3 N-nosyl-3-bromo-pyrrole 
• 172100-29-7 3-bromo-1H-pyrrol-1-amine 
• 214360-77-7 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1H-pyrrole 
• 1071444-90-0 C₂₃H₂₀N₂O₃ 
• 18159-13-2 1-benzyl-3-bromo-1H-pyrrole 

Relevant academic research and scientific papers

MALT1 INHIBITORS AND USES THEREOF

The invention provides compounds of formula (I) wherein R1, R2, R3, R4 and R5 are as defined in the specification which are potent inhibitors of the enzyme MALT1 and are useful in the treatment of autoimmune disorders and diseases and as an immunooncology approach to the treatment of cancer, especially bladder cancer, colon cancer, hepatocellular cancer and small cell or non-small cell lung cancer.

Silylpyrrole Oxidation En Route to Saxitoxin Congeners including 11-Saxitoxinethanoic Acid

Saxitoxin (STX) is the archetype of a large family (>50) of architecturally distinct, bisguanidinium natural products. Among this collection of isolates, two members, 11-saxitoxinethanoic acid (11-SEA) and zetekitoxin AB (ZTX), are unique, bearing carbon substitution at C11. A desire to efficiently access these compounds has motivated the development of new tactical approaches to a late-stage C11-ketone intermediate 26, designed to enable C–C bond formation using any one of a number of possible reaction technologies. Highlights of the synthesis of 26 include a metal-free, silylpyrrole oxidative dearomatization reaction and a vinylsilane epoxidation–rearrangement cascade to generate the requisite ketone. Nucleophilic addition to 26 makes possible the preparation of unnatural C11-substituted STXs. Olefination of this ketone is also demonstrated and, when followed by a redox-neutral isomerization reaction, affords 11-SEA.

Metal-Free Directed C?H Borylation of Pyrroles

Robust strategies to enable the rapid construction of complex organoboronates in selective, practical, low-cost, and environmentally friendly modes remain conspicuously underdeveloped. Here, we develop a general strategy for the site-selective C?H borylation of pyrroles by using only BBr3 directed by pivaloyl groups, avoiding the use of any metal. The site-selectivity is generally dominated by chelation and electronic effects, thus forming diverse C2-borylated pyrroles against the steric effect. The formed products can readily engage in downstream transformations, enabling a step-economic process to access drugs such as Lipitor. DFT calculations (wB97X-D) demonstrate the preferred positional selectivity of this reaction.

S1P3 ANTAGONISTS

The present invention relates to antagonists of the S1P3 receptor formula (A) as herein described and pharmaceutical compositions thereof. The compounds of formula (A) are useful in the preparation of a medicament, in particular for the treatment of Alzhe

SIP3 antagonists

The present invention relates to antagonists of the S1P3 receptor formula (A) as herein described and pharmaceutical compositions thereof. The compounds of formula (A) are useful in the preparation of a medicament, in particular for the treatment of Alzheimer's disease.

Highly efficient monophosphine-based catalyst for the palladium-catalyzed Suzuki-Miyaura reaction of heteroaryl halides and heteroaryl boronic acids and esters

A highly active and efficient catalyst system derived from a palladium precatalyst and monophosphine ligands 1 or 2 for the Suzuki-Miyaura cross-coupling reaction of heteroaryl boronic acids and esters has been developed. This method allows for the preparation of a wide variety of heterobiaryls in good to excellent yields and displays a high level of activity for the coupling of heteroaryl chlorides as well as hindered aryl and heteroaryl halides. Specific factors that govern the efficacy of the transformation for certain heterocyclic motifs were also investigated.

Synthesis and characterization of partially β-fluorinated 5,10,15,20-tetraphenylporphyrins and some derivatives

The synthesis of partially β-fluorinated meso-tetraphenylporphyrins using Lindsey conditions, has been examined, starting either from 3,4-difluoro-1H-pyrrole or from 3-fluoro-1H-pyrrole. In the case of the first synthon, condensation with pyrrole and benzaldehyde afforded a mixture of porphyrins of general formula β-FnTPP (n=0,2,4,6,8) displaying linearly correlated spectroscopic and electrochemical properties. With the second synthon, condensation with benzaldehyde produced an unresolvable mixture of β-tetrafluoroporphyrins presenting spectroscopic and electrochemical properties in coherence with those observed in the first case. Preliminarily, the synthesis and isolation of the hitherto unknown 3-fluoro-1H-pyrrole has been approached via several methods.

Highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles: A formal total synthesis of lukianol A

A combined use of α-lithiation and nucleophilic substitutions of N,N- dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide 8c led to several 2-substituted 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamides. Utilizing the β-effect of a trimethylsilyl group, a highly regioselective synthesis of 2,3,4-trisubstituted 1H-pyrroles 23 and 34 was accomplished. The marine natural product lukianol A (3) was prepared utilizing this strategy.

N-(Triisopropylsilyl)pyrrole. A Progenitor "Par Excellence" of 3-Substituted Pyrroles

A very effective strategy has been devised for the synthesis of 3-substituted pyrroles based on the use of the triisopropylsilyl (TIPS) moiety as a sterically demanding nitrogen substituent to obstruct the attack of electrophilic reagents at the α positions. 1-(Triisopropylsilyl)pyrrole (1) undergoes highly preferential kinetic electrophilic substitution at the β position with a variety of electrophiles (Br+, I+, NO2+, RCO+, etc.) and fluoride ion induced desilylation of the products provides the corresponding 3-substituted pyrroles in good overall yields.Competitive trifluoroacetylation experiments demonstrate that substitution of TIPS-pyrrole at the α positions is decelerated by a factor of >104, vs pyrrole at the same sites, without affecting reactivity at the β positions. 1-(Triisopropylsilyl)-3-bromopyrrole (2) is readily converted into the 3-lithio compound 44 by bromine-lithium interchange with alkyllithium reagents.This previously unavailable, formal equivalent of 3-lithiopyrrole is itself an excellent source of a wide range of β-substituted pyrroles, many of which would not be directly preparable from 1.TIPS-pyrrole can be 3,4-dihalogenated and these compounds undergo sequential halogen-metal interchange trapping reactions.This process is exemplified by an efficient, three-step synthesis of the antibiotic verrucarin E (63) from the dibromo compound (5).

β-SUBSTITUTED PYRROLES VIA ELECTROPHILIC SUBSTITUTION OF N-TRIISOPROPYLSILYLPYRROLE

N-Triisopropylsilylpyrrole undergoes predominant or exclusive kinetic electrophilic substitution at C-3, and the compounds obtained thereby, upon desilylation with tetra-n-butylammonium fluoride, give 3-substituted pyrroles in good overall yields.