2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile

Base Information

• Chemical Name: 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile
• CAS No.: 301296-47-9
• Molecular Formula: C₂₇H₂₈N₄O₃
• Molecular Weight: 456.544
• Mol file: 301296-47-9.mol

Synonyms:2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile

Chemical Property of 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile

There total 15 articles about 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile 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:

4-bromo-3-fluorotoluene (452-74-4) → 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile (301296-47-9)

Guidance literature:

Multi-step reaction with 11 steps

1.1: 88 percent / aq. KMnO₄; pyridine / 90 °C

2.1: 98 percent / borane-THF complex / tetrahydrofuran / 10 - 20 °C

3.1: 75 percent / Pd(PPh₃)4 / dimethylformamide / 18 h / 95 °C

4.1: 90 percent / Et₃N; DMSO; pyridine*SO₃ / CH₂Cl₂ / 2 h / 5 - 20 °C

5.1: EtMgBr / CH₂Cl₂ / 3 h / 20 °C

5.2: 98 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

6.1: 100 percent / pyridine / dimethylformamide / 3 h

7.1: ethyl acetate / 60 °C

8.1: 0.838 g / MeOH / 1 h / Heating

9.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

10.1: SOCl₂ / 2 h / 20 °C

10.2: 70 percent / NH₃ gas / CHCl₃ / 16 h / -78 - 20 °C

11.1: KF*Al₂O₃; 18-crown-6 / acetonitrile / Heating

With pyridine; methanol; sodium hydroxide; potassium permanganate; potassium fluoride on basic alumina; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; borane-THF; 18-crown-6 ether; ethylmagnesium bromide; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 4.1: Swern oxidation / 5.2: Grignard reaction;

DOI:10.1021/jm020587n

Reference yield:

4-bromo-3-fluorobenzyl alcohol (222978-01-0) → 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile (301296-47-9)

Guidance literature:

Multi-step reaction with 9 steps

1.1: 75 percent / Pd(PPh₃)4 / dimethylformamide / 18 h / 95 °C

2.1: 90 percent / Et₃N; DMSO; pyridine*SO₃ / CH₂Cl₂ / 2 h / 5 - 20 °C

3.1: EtMgBr / CH₂Cl₂ / 3 h / 20 °C

3.2: 98 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

4.1: 100 percent / pyridine / dimethylformamide / 3 h

5.1: ethyl acetate / 60 °C

6.1: 0.838 g / MeOH / 1 h / Heating

7.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

8.1: SOCl₂ / 2 h / 20 °C

8.2: 70 percent / NH₃ gas / CHCl₃ / 16 h / -78 - 20 °C

9.1: KF*Al₂O₃; 18-crown-6 / acetonitrile / Heating

With pyridine; methanol; sodium hydroxide; potassium fluoride on basic alumina; tetrakis(triphenylphosphine) palladium⁽⁰⁾; thionyl chloride; 18-crown-6 ether; ethylmagnesium bromide; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 2.1: Swern oxidation / 3.2: Grignard reaction;

DOI:10.1021/jm020587n

Reference yield:

2-fluoro-4-(hydroxymethyl)benzonitrile (222978-02-1) → 2-[3-(3-Ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-(3-methyl-3H-imidazole-4-carbonyl)-benzonitrile (301296-47-9)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 90 percent / Et₃N; DMSO; pyridine*SO₃ / CH₂Cl₂ / 2 h / 5 - 20 °C

2.1: EtMgBr / CH₂Cl₂ / 3 h / 20 °C

2.2: 98 percent / CH₂Cl₂ / 2 h / -78 - 20 °C

3.1: 100 percent / pyridine / dimethylformamide / 3 h

4.1: ethyl acetate / 60 °C

5.1: 0.838 g / MeOH / 1 h / Heating

6.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C

7.1: SOCl₂ / 2 h / 20 °C

7.2: 70 percent / NH₃ gas / CHCl₃ / 16 h / -78 - 20 °C

8.1: KF*Al₂O₃; 18-crown-6 / acetonitrile / Heating

With pyridine; methanol; sodium hydroxide; potassium fluoride on basic alumina; thionyl chloride; 18-crown-6 ether; ethylmagnesium bromide; sulfur trioxide pyridine complex; dimethyl sulfoxide; triethylamine; In tetrahydrofuran; dichloromethane; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 1.1: Swern oxidation / 2.2: Grignard reaction;

DOI:10.1021/jm020587n

upstream raw materials:

3-Ethyl-hexahydro-3-(3-hydroxyphenyl)-1-methyl-2H-azepin-2-one

2-fluoro-4-[amino-(1-methyl-1H-imidazol-5-yl)methyl]benzonitrile

1-methyl-2-azepanone

2-Chloroanisole

Downstream raw materials:

2-[3-(3-ethyl-1-methyl-2-oxo-azepan-3-yl)-phenoxy]-4-[1-hydroxy-1-(3-methyl-3H-imidazol-4-yl)-ethyl]-benzonitrile