6-{N-[3-chloro-4-(2-hydroxy-1,2-oxaborolan-4-yl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Base Information

Chemical Name:6-{N-[3-chloro-4-(2-hydroxy-1,2-oxaborolan-4-yl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide
CAS No.:1423008-25-6
Molecular Formula:C₂₉H₂₇BClFN₂O₆S
Molecular Weight:596.872
Hs Code.:

6-{N-[3-chloro-4-(2-hydroxy-1,2-oxaborolan-4-yl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

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

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

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

There total 18 articles about 6-{N-[3-chloro-4-(2-hydroxy-1,2-oxaborolan-4-yl)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: 10.2%

: 1423008-27-8
6-(N-{3-chloro-4-[3-(methoxymethoxy)prop-1-en-2-yl]phenyl}methanesulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

: 1423008-25-6
6-{N-[3-chloro-4-(2-hydroxy-1,2-oxaborolan-4-yl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:: 6-(N-{3-chloro-4-[3-(methoxymethoxy)prop-1-en-2-yl]phenyl}methanesulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide; With bis(1,5-cyclooctadiene)diiridium(I) dichloride; In tetrahydrofuran; for 0.166667h; Inert atmosphere;

With 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane; In tetrahydrofuran; at 20 ℃; for 18h;

Reference yield: 10.2%

: 1423008-27-8
6-(N-{3-chloro-4-[3-(methoxymethoxy)prop-1-en-2-yl]phenyl}methanesulfonamido)-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

: 25015-63-8
4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane

: 1423008-25-6
6-{N-[3-chloro-4-(2-hydroxy-1,2-oxaborolan-4-yl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:: With bis(1,5-cyclooctadiene)diiridium(I) dichloride; n-butyl-diphenylphosphane; In tetrahydrofuran; at 20 ℃; for 18h; Inert atmosphere;

Reference yield:

: 106-51-4
p-benzoquinone

: 1423008-25-6
6-{N-[3-chloro-4-(2-hydroxy-1,2-oxaborolan-4-yl)phenyl]methanesulfonamido}-5-cyclopropyl-2-(4-fluorophenyl)-N-methyl-1-benzofuran-3-carboxamide

Guidance literature:: Multi-step reaction with 16 steps

1.1: zinc(II) chloride / methanol; diethyl ether / 7.5 h / 75 - 140 °C / Inert atmosphere

2.1: caesium carbonate / 1-methyl-pyrrolidin-2-one / 20 h / 60 °C

3.1: nitric acid / chloroform / 1 h / -15 - 0 °C

4.1: boron trichloride / dichloromethane / 0.5 h / -15 °C / Inert atmosphere

5.1: triethylamine; dmap / dichloromethane / 0.83 h / 0 °C / Cooling with ice; Inert atmosphere

6.1: potassium fluoride; sodium bromide; tetrakis(triphenylphosphine) palladium⁽⁰⁾ / toluene; water / 18 h / 100 °C / Inert atmosphere

7.1: palladium 10% on activated carbon; hydrogenchloride; hydrogen / water; ethyl acetate / 16 h / 21 °C

8.1: triethylamine / dichloromethane / 2 h / 0 °C

9.1: potassium hydroxide; water / ethanol / 1 h / Reflux

10.1: triethylamine; HATU / dichloromethane / 1 h / 20 °C

10.2: 4 h / Inert atmosphere

11.1: potassium carbonate / water; 1,2-dimethoxyethane / 88 h / 20 - 100 °C / Sealed tube

12.1: hydrogen; 5 % platinum carbon sulfide / tetrahydrofuran; methanol / 40 h / 2068.65 Torr

13.1: hydrogen bromide / acetonitrile; water / 1 h / Cooling with ice

13.2: 1.58 h / Cooling with ice

13.3: 0.75 h / 60 °C

14.1: triethylamine; 1-butyl-3-methylimidazolium Tetrafluoroborate; 1,3-bis-(diphenylphosphino)propane; palladium diacetate / dimethyl sulfoxide / 59 h / 135 °C / Sealed tube

15.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1.5 h / 20 °C

16.1: bis(1,5-cyclooctadiene)diiridium(I) dichloride / tetrahydrofuran / 0.17 h / Inert atmosphere

16.2: 18 h / 20 °C

With hydrogenchloride; dmap; potassium fluoride; tetrakis(triphenylphosphine) palladium⁽⁰⁾; bis(1,5-cyclooctadiene)diiridium(I) dichloride; palladium 10% on activated carbon; 5 % platinum carbon sulfide; 1,3-bis-(diphenylphosphino)propane; water; hydrogen bromide; hydrogen; nitric acid; palladium diacetate; boron trichloride; potassium carbonate; caesium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; 1-butyl-3-methylimidazolium Tetrafluoroborate; sodium bromide; potassium hydroxide; zinc(II) chloride; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; methanol; 1,2-dimethoxyethane; diethyl ether; ethanol; dichloromethane; chloroform; water; dimethyl sulfoxide; ethyl acetate; toluene; acetonitrile; 13.1: |Sandmeyer Reaction;