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

Base Information

• Chemical Name: 4-[3’-(1''H-imidazol-1''-yl)phenyl]-8-(4'''-iodophenyl)-7-methoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one
• CAS No.: 1453393-70-8
• Molecular Formula: C₂₅H₁₉IN₄O₂
• Molecular Weight: 534.356

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

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

Chemical Property:

Purity/Quality:

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

There total 13 articles about 4-[3’-(1''H-imidazol-1''-yl)phenyl]-8-(4'''-iodophenyl)-7-methoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one 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: 53.0%

4-[3’-(1''H-imidazol-1''-yl)phenyl]-7-methoxy-8-(4'''-(trimethylstannyl)phenyl)-2,3-dihydro-1H-1,5-benzodiazepin-2-one (1453394-04-1) → 4-[3’-(1''H-imidazol-1''-yl)phenyl]-8-(4'''-iodophenyl)-7-methoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one (1453393-70-8)

Guidance literature:

With hydrogenchloride; chloroamine-T; sodium iodide; sodium hydroxide; In ethanol; water; at 20 ℃; for 0.5h; pH=4 - 5;

DOI:10.1039/c3md00110e

Reference yield:

2-nitro-4-iodo-5-chloroaniline (335349-57-0) → 4-[3’-(1''H-imidazol-1''-yl)phenyl]-8-(4'''-iodophenyl)-7-methoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one (1453393-70-8)

Guidance literature:

Multi-step reaction with 9 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

7: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C

8: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 48 h / 90 °C / Inert atmosphere

9: sodium hydroxide; sodium iodide; hydrogenchloride; chloroamine-T / water; ethanol / 0.5 h / 20 °C / pH 4 - 5

With pyridine; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(II) chloride dihdyrate; chloroamine-T; potassium carbonate; triethylamine; trifluoroacetic acid; sodium iodide; potassium hydroxide; sodium hydroxide; In 1,4-dioxane; ethanol; 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-[3’-(1''H-imidazol-1''-yl)phenyl]-8-(4'''-iodophenyl)-7-methoxy-2,3-dihydro-1H-1,5-benzodiazepin-2-one (1453393-70-8)

Guidance literature:

Multi-step reaction with 10 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

8: trifluoroacetic acid / dichloromethane / 0.5 h / 0 - 20 °C

9: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / 1,4-dioxane / 48 h / 90 °C / Inert atmosphere

10: sodium hydroxide; sodium iodide; hydrogenchloride; chloroamine-T / water; ethanol / 0.5 h / 20 °C / pH 4 - 5

With pyridine; hydrogenchloride; dmap; tetrakis(triphenylphosphine) palladium⁽⁰⁾; tin(II) chloride dihdyrate; sodium acetate; chloroamine-T; Iodine monochloride; potassium carbonate; acetic acid; triethylamine; trifluoroacetic acid; sodium iodide; potassium hydroxide; sodium hydroxide; In 1,4-dioxane; ethanol; 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

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