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901778

Sigma-Aldrich

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

Synonym(s):

Aryl halide chemistry informer library compound X2

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About This Item

Empirical Formula (Hill Notation):
C15H14BrN3O3
CAS Number:
78756-37-3
Molecular Weight:
364.19
MDL number:
MFCD12911997
UNSPSC Code:
12352101
NACRES:
NA.22

form

powder or crystals

mp

190-193 °C

SMILES string

BrC1=CC=C2C(C(N(C)CC3=C(C(OCC)=O)N=CN32)=O)=C1

InChI

1S/C15H14BrN3O3/c1-3-22-15(21)13-12-7-18(2)14(20)10-6-9(16)4-5-11(10)19(12)8-17-13/h4-6,8H,3,7H2,1-2H3

InChI key

NFMFVESVKLVYJR-UHFFFAOYSA-N

Application

This product is Informer compound X2 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 analyze a reactions′s successes and shortcomings among different methods and various research teams. It may also be used to faciliate deeper method development for performance or utlity.

Caution

Not Fully Tested.

Other Notes

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

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

3.Aryl amination using ligand-free Ni(II) salts and photoredox catalysis

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Storage Class Code

13 - Non Combustible Solids

WGK

WGK 3

Flash Point(C)

Not applicable

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Emily B Corcoran et al.
Science (New York, N.Y.), 353(6296), 279-283 (2016-06-25)
Over the past two decades, there have been major developments in transition metal-catalyzed aminations of aryl halides to form anilines, a common structure found in drug agents, natural product isolates, and fine chemicals. Many of these approaches have enabled highly
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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