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901719

Sigma-Aldrich

Benzyl (S)-2-(5-bromo-1H-indole-3-carbonyl)pyrrolidine-1-carboxylate

Synonym(s):

Aryl halide chemistry informer library compound X5

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About This Item

Empirical Formula (Hill Notation):
C21H19BrN2O3
CAS Number:
199659-03-5
Molecular Weight:
427.29
UNSPSC Code:
12352101
NACRES:
NA.22

form

powder or crystals

mp

191 °C

Application

This product is Informer compound X5 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 reaction′s successes and shortcomings among different methods and various research teams. It may also be used to facilitate deeper method development for performance or utility.

Caution

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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Description
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901723

Methyl 2-(9-bromo-2,3-dioxo-2,3,6,7-tetrahydro-1H,5H-pyrido[1,2,3-de]quinoxalin-5-yl)acetate, ≥90%

901724

3-((5-Bromopyridin-2-yl)oxy)-5,5-dimethyl-4-(4-(methylsulfonyl)phenyl)furan-2(5H)-one

901725

1-(Tert-butyl) 2-methyl (2S,4R)-4-((4-bromo-7-fluoroisoindoline-2-carbonyl)oxy)pyrrolidine-1,2-dicarboxylate

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

901733

(R)-2-(5-Bromo-4-(4-chlorobenzyl)-7-fluoro-1,2,3,4-tetrahydrocyclopenta[b]indol-3-yl)acetic acid

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

901753

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

901782

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

901752

N-(tert-Butyl)-4′-((6-iodo-4-oxo-2-propylquinazolin-3(4H)-yl)methyl)-[1,1′-biphenyl]-2-sulfonamide

901781

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

Ethyl 8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate

901744

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

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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
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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