4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene

Base Information

• Chemical Name: 4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene
• CAS No.: 1453393-97-9
• Molecular Formula: C₃₀H₂₉BrN₄O₅
• Molecular Weight: 605.488
• Mol file: 1453393-97-9.mol

Synonyms:4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene

Chemical Property of 4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene

There total 9 articles about 4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene 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: 73.0%

3-(3-Imidazol-1-yl-phenyl)-3-oxo-propionic Acid tert-butyl Ester (335255-84-0) + 2-amino-4-(4’-bromophenyl)-1-(tert-butoxycarbonylamino)-5-methoxybenzene (1453393-52-6) → 4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene (1453393-97-9)

Guidance literature:

In toluene; for 4h; Reflux;

DOI:10.1039/c3md00110e

Reference yield:

2-nitro-4-iodo-5-chloroaniline (335349-57-0) → 4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene (1453393-97-9)

Guidance literature:

Multi-step reaction with 6 steps

1: potassium hydroxide / dimethyl sulfoxide / 6 h / 60 °C

2: triethylamine; dmap / dichloromethane / 18 h / 20 °C

3: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

4: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 1.5 h / 110 °C

5: tin(II) chloride dihdyrate; pyridine / ethyl acetate / 17 h / 20 °C

6: toluene / 4 h / Reflux

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(II) chloride dihdyrate; potassium carbonate; triethylamine; trifluoroacetic acid; potassium hydroxide; In dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; 4: |Suzuki-Miyaura Coupling;

DOI:10.1039/c3md00110e

Reference yield:

5-chloro-2-nitroaniline (1635-61-6) → 4-(4''''-bromophenyl)-1-(tert-butoxycarbonylamino)-2-{3’-[3''-(1'''H-imidazol-1'''-yl)phenyl]-3’-oxopropanamido}-5-methoxybenzene (1453393-97-9)

Guidance literature:

Multi-step reaction with 7 steps

1: Iodine monochloride; acetic acid; sodium acetate / 3 h / 80 °C

2: potassium hydroxide / dimethyl sulfoxide / 6 h / 60 °C

3: triethylamine; dmap / dichloromethane / 18 h / 20 °C

4: trifluoroacetic acid / dichloromethane / 2 h / 0 - 20 °C

5: potassium carbonate; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / water; N,N-dimethyl-formamide / 1.5 h / 110 °C

6: tin(II) chloride dihdyrate; pyridine / ethyl acetate / 17 h / 20 °C

7: toluene / 4 h / Reflux

With pyridine; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(II) chloride dihdyrate; sodium acetate; Iodine monochloride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; potassium hydroxide; In dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; 5: |Suzuki-Miyaura Coupling;

DOI:10.1039/c3md00110e

upstream raw materials:

5-chloro-2-nitroaniline

2-nitro-4-iodo-5-chloroaniline

4-iodo-5-methoxy-2-nitroaniline

1-(tert-butoxycarbonylamino)-4-iodo-5-methoxy-2-nitrobenzene

Downstream raw materials:

8-(4'''-bromophenyl)-4-[3’-(1''H-imidazol-1''yl)phenyl]-7-methoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one

4-[3’-(1''H-imidazol-1''-yl)phenyl]-8-(4'''-iodophenyl)-7-methoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one

4-[3’-(1''H-imidazol-1''-yl)phenyl]-7-methoxy-8-(4'''-(trimethylstannyl)phenyl)-2,3-dihydro-1H-1,5-benzodiazepin-2-one