6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde

Base Information

• Chemical Name: 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde
• CAS No.: 1426082-13-4
• Molecular Formula: C₂₇H₂₄N₄O₂S
• Molecular Weight: 468.579
• Mol file: 1426082-13-4.mol

Synonyms:6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde

Chemical Property of 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde

There total 8 articles about 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde 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: 51.0%

{2-[4-(4-bromo-5-pyridin-4-yl-1H-imidazol-2-yl)-phenoxy]-ethyl}-dimethyl-amine (1251931-23-3) + 6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophene-3-carbaldehyde (1426082-56-5) → 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde (1426082-13-4)

Guidance literature:

With palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; water; for 2h; Reflux;

DOI:10.1016/j.bmc.2012.12.035

Reference yield:

{2-[4-(4-bromo-1-methoxymethyl-5-pyridin-4-yl-1H-imidazol-2-yl)-phenoxy]-ethyl}-dimethyl-amine (1251931-22-2) → 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde (1426082-13-4)

Guidance literature:

Multi-step reaction with 2 steps

1: hydrogenchloride; water / 60 °C

2: potassium carbonate; triphenylphosphine; palladium diacetate / water; 1,2-dimethoxyethane / 2 h / Reflux

With hydrogenchloride; water; palladium diacetate; potassium carbonate; triphenylphosphine; In 1,2-dimethoxyethane; water; 2: |Suzuki Coupling;

DOI:10.1016/j.bmc.2012.12.035

Reference yield:

4-bromo-2-fluorobenzaldehyde (57848-46-1) → 6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophene-3-carbaldehyde (1426082-13-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: potassium carbonate / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

1.2: 5.5 h / 60 °C

2.1: potassium hydroxide / water; ethanol / 1.5 h / Reflux

3.1: copper; quinoline / 2 h / 185 °C

4.1: N-Bromosuccinimide; acetic acid / chloroform / 20 °C / Cooling with ice

5.1: n-butyllithium / diethyl ether; hexane / 1.25 h / -40 °C

5.2: 4 h / -70 °C

6.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 90 °C

7.1: potassium carbonate; triphenylphosphine; palladium diacetate / water; 1,2-dimethoxyethane / 2 h / Reflux

With quinoline; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-Bromosuccinimide; n-butyllithium; potassium acetate; palladium diacetate; copper; potassium carbonate; acetic acid; triphenylphosphine; potassium hydroxide; In 1,2-dimethoxyethane; diethyl ether; ethanol; hexane; chloroform; water; N,N-dimethyl-formamide; 7.1: |Suzuki Coupling;

DOI:10.1016/j.bmc.2012.12.035

upstream raw materials:

{2-[4-(4-bromo-1-methoxymethyl-5-pyridin-4-yl-1H-imidazol-2-yl)-phenoxy]-ethyl}-dimethyl-amine

{2-[4-(4-bromo-5-pyridin-4-yl-1H-imidazol-2-yl)-phenoxy]-ethyl}-dimethyl-amine

6-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzo[b]thiophene-3-carbaldehyde

4-bromo-2-fluorobenzaldehyde

Downstream raw materials:

(6-{2-[4-(2-dimethylamino-ethoxy)-phenyl]-5-pyridin-4-yl-3H-imidazol-4-yl}-benzo[b]thiophen-3-yl)-methanol