6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid

Base Information

• Chemical Name: 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid
• CAS No.: 1586025-50-4
• Molecular Formula: C₂₂H₂₃NO₅S
• Molecular Weight: 413.494

Synonyms:6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid

Chemical Property of 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid

Chemical Property:

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Technology Process of 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid

There total 5 articles about 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid 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: 46.0%

methyl 7-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoate (1586025-48-0) → 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid (1586025-50-4)

Guidance literature:

methyl 7-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoate; With boron tribromide; In dichloromethane; at 0 - 20 ℃; for 20h; Inert atmosphere;

With hydrogenchloride; In dichloromethane; water; Inert atmosphere;

DOI:10.1002/cmdc.201300270

Reference yield:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene (63675-74-1) → 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid (1586025-50-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: bromine / chloroform / 0.17 h / 50 °C / Inert atmosphere

2.1: n-butyllithium / hexane / 2 h / -78 °C / Inert atmosphere

2.2: Inert atmosphere

2.3: Inert atmosphere

3.1: thionyl chloride / toluene / 2 h / Reflux; Inert atmosphere

4.1: triethylamine / dichloromethane / 24 h / 0 °C / Inert atmosphere

5.1: boron tribromide / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

5.2: Inert atmosphere

With n-butyllithium; thionyl chloride; bromine; boron tribromide; triethylamine; In hexane; dichloromethane; chloroform; toluene;

DOI:10.1002/cmdc.201300270

Reference yield:

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate (186787-88-2) → 6-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoic acid (1586025-50-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine / dichloromethane / 24 h / 0 °C / Inert atmosphere

2.1: boron tribromide / dichloromethane / 20 h / 0 - 20 °C / Inert atmosphere

2.2: Inert atmosphere

With boron tribromide; triethylamine; In dichloromethane;

DOI:10.1002/cmdc.201300270

upstream raw materials:

2-(4'-methoxyphenyl)-6-methoxybenzothiophene

methyl 6-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)hexanoate

3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene

methyl 7-(6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoate

Downstream raw materials:

methyl 7-(6-hydroxy-2-(4-hydroxyphenyl)benzo[b]thiophene-3-carboxamido)heptanoate

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