ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate

Base Information

• Chemical Name: ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate
• CAS No.: 1395059-98-9
• Molecular Formula: C₂₇H₂₅NO₃
• Molecular Weight: 411.5
• Mol file: 1395059-98-9.mol

Synonyms:ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate

Chemical Property of ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate

There total 10 articles about ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate 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: 61.0%

3-iodobenzoic acid methyl ester (58313-23-8) + 2-ethyl-5,11-dihydro-5-methyl-11-methylene-8-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-6H-dibenz[b,e]azepin-6-one (1395059-97-8) → ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate (1395059-98-9)

Guidance literature:

With potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In N,N-dimethyl-formamide; at 120 ℃; for 3h; Inert atmosphere;

DOI:10.1021/jm3002394

Reference yield:

5-hydroxy-2-iodo-benzoic acid (57772-57-3) → ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate (1395059-98-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: potassium carbonate / acetone / 5 h / Reflux

2.1: sodium hydroxide / water; methanol / 2 h / Reflux

3.1: Vilsmeier reagent / dichloromethane / 0.5 h / 0 - 20 °C

3.2: 12 h / 0 - 20 °C

4.1: sodium hydride / N,N-dimethyl-formamide / 6.5 h / 0 - 20 °C

5.1: palladium diacetate; triphenylphosphine; sodium acetate / N,N-dimethyl-formamide / 8 h / 100 °C / Inert atmosphere

6.1: boron tribromide / dichloromethane / 3 h / 0 °C / Inert atmosphere

7.1: pyridine / dichloromethane / 2 h / 0 - 20 °C

8.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 3 h / 120 °C / Inert atmosphere

9.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Vilsmeier reagent; potassium acetate; sodium acetate; palladium diacetate; boron tribromide; sodium hydride; potassium carbonate; triphenylphosphine; sodium hydroxide; In 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 5.1: |Heck Reaction;

DOI:10.1021/jm3002394

Reference yield:

2-bromine-4-ethylaniline (38678-86-3) → ethyl 3-(5,11-dihydro-2-ethyl-5-methyl-11-methylene-6-oxodibenz[b,e]azepin-8-yl)benzoate (1395059-98-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene / 6 h / 100 °C / Inert atmosphere

2.1: Vilsmeier reagent / dichloromethane / 0.5 h / 0 - 20 °C

2.2: 12 h / 0 - 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide / 6.5 h / 0 - 20 °C

4.1: palladium diacetate; triphenylphosphine; sodium acetate / N,N-dimethyl-formamide / 8 h / 100 °C / Inert atmosphere

5.1: boron tribromide / dichloromethane / 3 h / 0 °C / Inert atmosphere

6.1: pyridine / dichloromethane / 2 h / 0 - 20 °C

7.1: bis-triphenylphosphine-palladium(II) chloride; potassium acetate / 1,4-dioxane / 3 h / 120 °C / Inert atmosphere

8.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; potassium phosphate / N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere

With pyridine; bis-triphenylphosphine-palladium(II) chloride; potassium phosphate; tetrakis(triphenylphosphine) palladium⁽⁰⁾; Vilsmeier reagent; potassium acetate; sodium acetate; palladium diacetate; boron tribromide; sodium hydride; triphenylphosphine; In 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; toluene; 4.1: |Heck Reaction;

DOI:10.1021/jm3002394

upstream raw materials:

2-bromine-4-ethylaniline

4-ethyl-2-vinylaniline

2-amino-5-hydroxybenzoic acid

5-hydroxy-2-iodo-benzoic acid

Downstream raw materials:

C₂₅H₂₁NO₃