2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

Base Information

• Chemical Name: 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline
• CAS No.: 1126425-86-2
• Molecular Formula: C₁₉H₂₉ClN₂Si
• Molecular Weight: 348.991
• Mol file: 1126425-86-2.mol

Synonyms:2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

Chemical Property of 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline

There total 4 articles about 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline 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: 82.0%

2-bromo-6-chloroaniline (59772-49-5) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-86-2)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In water; butan-1-ol; at 35 ℃; for 12h; Inert atmosphere;

DOI:10.1021/ol8026957

Reference yield: 81.0%

2-chloro-6-iodobenzoic acid (13420-63-8) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-86-2) + C19H29ClN(15)NSi

Guidance literature:

2-chloro-6-iodobenzoic acid; With sulfuric acid; at 60 ℃; for 1h; Inert atmosphere;

With [⁽¹⁵⁾N]sodium azide; at 20 ℃; for 42h; Inert atmosphere;

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole; With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In water; butan-1-ol; at 20 ℃; for 16h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00098

Reference yield: 75.0%

2-chloro-6-iodoaniline (84483-28-3) + 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole (365564-11-0) → 2-chloro-6-(1-(triisopropylsilyl)-1H-pyrrol-3-yl)aniline (1126425-86-2)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; potassium phosphate; palladium diacetate; In water; butan-1-ol; at 20 ℃; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00098

upstream raw materials:

2-bromo-6-chloroaniline

3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-(triisopropylsilyl)pyrrole

2-chloro-6-iodoaniline

2-chloro-6-iodobenzoic acid

Downstream raw materials:

3-(3'-chloro-2'-aminophenyl)pyrrole

Refernces

• 1、 Morrison, Matthew D.,Hanthorn, Jason J.,Pratt, Derek A.. "Synthesis of pyrrolnitrin and related halogenated phenylpyrroles". supporting information; experimental part. p. 1051 - 1054. Retrieved 2009/07/18.