Ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate

Name: Ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11<I>H</I>-benzo[5,6]cyclohepta[1,2-<I>b</I>]pyridin-11-ylidene)piperidine-1-carboxylate
Brand: ALDRICH
Price: 123 USD

Synonym(s):

Aryl halide chemistry informer library compound X6

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About This Item

Empirical Formula (Hill Notation):

C₂₂H₂₂BrClN₂O₂

CAS Number:

165740-12-5

Molecular Weight:

461.78

UNSPSC Code:

12352101

NACRES:

NA.22

MDL number:

MFCD20260305

Key Documents

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SMILES string

Brc1cnc2c(c1)CCc3c(ccc(c3)Cl)C2=C4CCN(CC4)C(=O)OCC

InChI key

KEMBMHKAPVBZHC-UHFFFAOYSA-N

form

powder

mp

355 °C

functional group

bromo
chloro

Related Categories

Halogenated Heterocycles

Heterocyclic Building Blocks

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This Item	901719	901747	901779
Sigma-Aldrich 901729 Ethyl 4-(3-bromo-8-chloro-5,6-dihydro-11H-benzo[5,6]cyclohepta[1,2-b]pyridin-11-ylidene)piperidine-1-carboxylate	Sigma-Aldrich 901719 Benzyl (S)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate	Sigma-Aldrich 901747 7-(3-Bromo-4-methoxybenzyl)-1-ethyl-8-(((1R,2R)-2-hydroxycyclopentyl)amino)-3-(2-hydroxyethyl)-3,7-dihydro-1H-purine-2,6-dione	Sigma-Aldrich 901779 4-((6-Amino-5-bromo-2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile
form powder	form powder or crystals	form powder or crystals	form powder
mp 355 °C	mp 191 °C	mp -	mp 246-251 °C
functional group bromo	functional group -	functional group -	functional group bromo, nitrile

Application

This product is Informer compound X6 of the Aryl Halide Chemistry Informer Library developed by chemists at Merck & Co., Inc., Kenilworth, NJ, U.S., which contains 18 drug-like molecules representative of those encountered in complex synthesis. By screening a new reaction against the Informer Library, chemists can directly compare and analyse a reactions′ successes and shortcomings among different methods and various research teams. It may also be used to facilitate deeper method development for performance or utility.

Disclaimer

Not fully tested

Other Notes

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods, Chem. Sci., 2016, 7, 2604-2613

Synthesis of Complex Druglike Molecules by the Use of Highly Functionalized Bench-Stable Organozinc Reagents

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901735

1-Benzyl 2-methyl (2S,4R)-4-((4-bromoisoindoline-2-carbonyl)oxy)pyrrolidine-1,2-dicarboxylate

901783

Methyl 3-(3-(tert-butylthio)-1-(4-chlorobenzyl)-5-(quinolin-2-ylmethoxy)-1H-indol-2-yl)-2,2-dimethylpropanoate

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(S)-6-Chloro-4-(cyclopropylethynyl)-4-(trifluoromethyl)-1,4-dihydro-2H-benzo[d][1,3]oxazin-2-one

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tert-Butyl (R)-3-(2-acetamidopropan-2-yl)-6-chloro-5-methyl-2,3-dihydrospiro[indene-1,4′-piperidine]-1′-carboxylate

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tert-Butyl (S,Z)-(4-(4-bromothiophen-2-yl)-1,4-dimethyl-6-oxotetrahydropyrimidin-2(1H)-ylidene)carbamate

901749

(R)-5-((1H-1,2,3-Triazol-1-yl)methyl)-3-(3-fluoro-4-iodophenyl)oxazolidin-2-one

901747

7-(3-Bromo-4-methoxybenzyl)-1-ethyl-8-(((1R,2R)-2-hydroxycyclopentyl)amino)-3-(2-hydroxyethyl)-3,7-dihydro-1H-purine-2,6-dione

901779

4-((6-Amino-5-bromo-2-((4-cyanophenyl)amino)pyrimidin-4-yl)oxy)-3,5-dimethylbenzonitrile

901745

5-Bromo-N-(4-fluorobenzyl)-8-hydroxy-1,6-naphthyridine-7-carboxamide, ≥90%

901778

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901744

2-(5-(3-(4-(2-Bromo-5-fluorophenoxy)piperidin-1-yl)isoxazol-5-yl)-2H-tetrazol-2-yl)acetic acid

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Synthesis of Complex Druglike Molecules by the Use of Highly Functionalized Bench-Stable Organozinc Reagents.

Thomas J Greshock et al.

Angewandte Chemie (International ed. in English), 55(44), 13714-13718 (2016-10-22)

The reactivity of a representative set of 17 organozinc pivalates with 18 polyfunctional druglike electrophiles (informers) in Negishi cross-coupling reactions was evaluated by high-throughput experimentation protocols. The high-fidelity scaleup of successful reactions in parallel enabled the isolation of sufficient material

Chemistry informer libraries: a chemoinformatics enabled approach to evaluate and advance synthetic methods.

Peter S Kutchukian et al.

Chemical science, 7(4), 2604-2613 (2016-04-21)

Major new advances in synthetic chemistry methods are typically reported using simple, non-standardized reaction substrates, and reaction failures are rarely documented. This makes the evaluation and choice of a synthetic method difficult. We report a standardized complex molecule diagnostic approach

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