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

Base Information

• Chemical Name: Ethyl 8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate
• CAS No.: 78756-37-3
• Molecular Formula: C₁₅H₁₄BrN₃O₃
• Molecular Weight: 364.198
• DSSTox Substance ID: DTXSID001121120
• Nikkaji Number: J921.790H
• ChEMBL ID: CHEMBL133219
• Mol file: 78756-37-3.mol

Synonyms:78756-37-3;Ethyl 8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate;CHEMBL133219;SCHEMBL8235506;DTXSID001121120;BDBM50067422;ethyl 8-bromo-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate;5-Methyl-6-oxo-8-bromo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester;8-bromo-5,6-dihydro-5-methyl-6-oxo-4H-Imidazo[1,5-a][1,4]benzodiazepine-3-carboxylic acid ethyl ester;8-Bromo-5-methyl-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester;Ethyl 8-bromo-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate;Ethyl8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate

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

Chemical Property:

• Melting Point: 192-193 °C
• Boiling Point: 567.3±50.0 °C(Predicted)
• Density: 1.60±0.1 g/cm3(Predicted)
• XLogP3: 1.6
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 363.02185
• Heavy Atom Count: 22
• Complexity: 461

Purity/Quality:

98%,99%, ^*data from raw suppliers

Ethyl8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCOC(=O)C1=C2CN(C(=O)C3=C(N2C=N1)C=CC(=C3)Br)C
• Uses: 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.

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

There total 8 articles about Ethyl 8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 40.0%

Ethyl isocyanoacetate (2999-46-4) + 7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione (78756-36-2) → ethyl 8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate (78756-37-3)

Guidance literature:

7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione; With potassium tert-butylate; In tetrahydrofuran; at 0 ℃; for 0.333333h; Inert atmosphere;

With diethyl chlorophosphate; In tetrahydrofuran; at -35 - 0 ℃; for 0.5h; Inert atmosphere;

Ethyl isocyanoacetate; In tetrahydrofuran; at -78 - 20 ℃; for 4h; Inert atmosphere;

DOI:10.24820/ARK.5550190.P011.396

Reference yield: 40.0%

ethyl 2-cyanoacetate (105-56-6) + 7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione (78756-36-2) → ethyl 8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate (78756-37-3)

Guidance literature:

7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione; With diethyl chlorophosphate; lithium diisopropyl amide; In tetrahydrofuran; at 0 ℃;

ethyl 2-cyanoacetate; With lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jm034164c

Reference yield:

4-methyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-dione (3415-35-8) → ethyl 8-bromo-5-methyl-6-oxo-5,6-dihydro-4H-benzo[f]imidazo[1,5-a][1,4]diazepine-3-carboxylate (78756-37-3)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 80 percent / Br₂; NaOAc; AcOH / 20 °C

2.1: LDA; ClPO(OEt)2 / tetrahydrofuran / 0 °C

2.2: 40 percent / LDA / tetrahydrofuran

With bromine; sodium acetate; diethyl chlorophosphate; acetic acid; lithium diisopropyl amide; In tetrahydrofuran;

DOI:10.1021/jm034164c

upstream raw materials:

ethyl 2-cyanoacetate

7-bromo-3,4-dihydro-4-methyl-2H-1,4-benzodiazepine-2,5-(1H)-dione

4-methyl-3H-1,4-benzodiazepine-2,5-(1H,4H)-dione

Ethyl isocyanoacetate

Downstream raw materials:

XLi-093

C₂F₃O₂^(1-)*C₂₁H₁₉IN₃O₃⁽¹⁺⁾

8-hydroxy-5-methyl-6-oxo-5,6-dihydro-4H-2,5,10b-triaza-benzo[e]azulene-3-carboxylic acid ethyl ester

Refernces

• 1、 Yang, Liu,Huang, Zhiyan,Li, Gang,Zhang, Wei,Cao, Rui,Wang, Chao,Xiao, Jianliang,Xue, Dong. "Synthesis of Phenols: Organophotoredox/Nickel Dual Catalytic Hydroxylation of Aryl Halides with Water". supporting information. p. 1968 - 1972. Retrieved 2018/02/06.
• 2、 -. "METHOD FOR PREPARATION OF FLUORINE-18-LABELED FLUMAZENIL USING DIARYLIODONIUM SALT PRECURSOR". . . Retrieved 2014/04/03.