(E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol

Base Information

• Chemical Name: (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol
• CAS No.: 1622307-71-4
• Molecular Formula: C₂₄H₁₈N₄O₃S
• Molecular Weight: 442.498
• Mol file: 1622307-71-4.mol

Synonyms:(E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol

Chemical Property of (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol

There total 10 articles about (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol 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: 35.0%

(E)-5-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)styryl)-1-methyl-1H-tetrazole (1622309-29-8) → (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol (1622307-71-4)

Guidance literature:

With boron tribromide; trifluoroacetic acid; In n-heptane; dichloromethane;

Reference yield:

2-(4'-methoxyphenyl)-3-bromo-6-methoxybenzo[b]thiophene S-oxide (182133-00-2) → (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol (1622307-71-4)

Guidance literature:

Multi-step reaction with 7 steps

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C

1.2: 18 h / 80 °C

2.1: triphenylphosphine; chloro-trimethyl-silane / tetrahydrofuran / 18 h / 75 °C

3.1: lithium hydroxide / tetrahydrofuran; methanol; water / 1 h / 20 °C

4.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h

4.2: 0.5 h / 20 °C

5.1: di(n-butyl)tin oxide; trimethylsilylazide / 1,2-dimethoxyethane / 1 h / 180 °C / Microwave irradiation

6.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C

7.1: boron tribromide / dichloromethane; hexane / 1 h / 20 °C

With chloro-trimethyl-silane; trimethylsilylazide; boron tribromide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.7b01682

Reference yield:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene (63675-74-1) → (E)-2-(4-hydroxyphenyl)-3-(4-(2-(1-methyl-1H-tetrazol-5-yl)vinyl)-phenoxy)benzo[b]thiophen-6-ol (1622307-71-4)

Guidance literature:

Multi-step reaction with 9 steps

1.1: N-Bromosuccinimide / tetrahydrofuran / 3 h / 0 - 25 °C

2.1: trifluoroacetic acid; dihydrogen peroxide / dichloromethane / 1.67 h / 20 °C

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C

3.2: 18 h / 80 °C

4.1: triphenylphosphine; chloro-trimethyl-silane / tetrahydrofuran / 18 h / 75 °C

5.1: lithium hydroxide / tetrahydrofuran; methanol; water / 1 h / 20 °C

6.1: N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 0.17 h

6.2: 0.5 h / 20 °C

7.1: di(n-butyl)tin oxide; trimethylsilylazide / 1,2-dimethoxyethane / 1 h / 180 °C / Microwave irradiation

8.1: potassium carbonate / N,N-dimethyl-formamide / 18 h / 20 °C

9.1: boron tribromide / dichloromethane; hexane / 1 h / 20 °C

With N-Bromosuccinimide; chloro-trimethyl-silane; trimethylsilylazide; dihydrogen peroxide; boron tribromide; sodium hydride; di(n-butyl)tin oxide; potassium carbonate; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; lithium hydroxide; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; water; N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.7b01682

upstream raw materials:

(E)-5-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)styryl)-2H-tetrazole

(E)-5-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)styryl)-1-methyl-1H-tetrazole

(E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)acrylate

(E)-methyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophen-3-yl)oxy)phenyl)acrylate