6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Base Information

Chemical Name:6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide
CAS No.:1423008-51-8
Molecular Formula:C₂₇H₂₃BrClFN₂O₅S
Molecular Weight:621.911
Hs Code.:

Synonyms:6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

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Chemical Property of 6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

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Technology Process of 6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

There total 21 articles about 6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide 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: 68.0%

: 1423007-86-6
methyl 2-bromo-3-chloro-5-{N-[5-cyclopropyl-2-(4-fluorophenyl)-3-(methylcarbamoyl)-1-benzofuran-6-yl]methanesulfonamido}benzoate

: 1423008-51-8
6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:: With lithium borohydride; In 2-methyltetrahydrofuran; methanol; at 10 - 23 ℃; for 2h;
DOI:10.1021/acs.joc.8b02269

Reference yield:

: 393-85-1
methyl 5-fluoro-2-nitrobenzoate

: 1423008-51-8
6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N,N,N,N,N-hexamethylphosphoric triamide / 72 h / 60 °C / Inert atmosphere

2.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 775.74 Torr

3.1: N-chloro-succinimide / acetonitrile / 1 h / 40 °C / Inert atmosphere

4.1: sodium nitrite; hydrogen bromide / acetonitrile; water / 0.5 h / 0 °C

4.2: 0.5 h / 0 - 50 °C

5.1: lithium borohydride; methanol / tetrahydrofuran / 1 h / 0 °C / Inert atmosphere

With methanol; N-chloro-succinimide; lithium borohydride; palladium 10% on activated carbon; hydrogen bromide; hydrogen; potassium carbonate; sodium nitrite; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetonitrile;

Reference yield:

: 691856-35-6
5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-6-(methylsulfonamido)benzofuran-3-carboxamide

: 1423008-51-8
6-{N-[4-bromo-3-chloro-5-(hydroxymethyl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium carbonate / N,N,N,N,N,N-hexamethylphosphoric triamide / 72 h / 60 °C

2.1: palladium 10% on activated carbon; hydrogen / methanol / 1.5 h / 775.74 Torr

3.1: N-chloro-succinimide / acetonitrile / 1 h / 40 °C

4.1: hydrogen bromide; sodium nitrite / acetonitrile; water / 0.5 h / 0 °C

4.2: 0.5 h / 50 °C

5.1: methanol; lithium borohydride / tetrahydrofuran / 2.08 h / -5 °C

With methanol; N-chloro-succinimide; lithium borohydride; palladium 10% on activated carbon; hydrogen bromide; hydrogen; potassium carbonate; sodium nitrite; In tetrahydrofuran; methanol; N,N,N,N,N,N-hexamethylphosphoric triamide; water; acetonitrile; 4.1: |Sandmeyer Reaction;