N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide

Base Information

• Chemical Name: N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide
• CAS No.: 284663-63-4
• Molecular Formula: C₁₈H₂₆N₂O₅SSi
• Molecular Weight: 410.566
• Mol file: 284663-63-4.mol

Synonyms:N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide

Chemical Property of N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide

There total 3 articles about N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide 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: 98.0%

4-methoxyphenylboronic acid (5720-07-0) + N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-iodo-1H-pyrrole-1-sulfonamide (284663-33-8) → N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide (284663-63-4)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium sulfate; In methanol; toluene; at 90 - 100 ℃; for 2h;

DOI:10.1021/jo9915224

Reference yield:

N-N-dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide (278167-17-2) → N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide (284663-63-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 - -60 °C

1.2: 58 percent / hexane; tetrahydrofuran / -60 - 20 °C

2.1: 100 percent / CF₃CO₂Ag; I₂ / tetrahydrofuran / 2 h / -78 °C

3.1: 98 percent / Pd(PPh₃)4; Na₂SO₄ / methanol; toluene / 2 h / 90 - 100 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; n-butyllithium; iodine; silver trifluoroacetate; sodium sulfate; In tetrahydrofuran; methanol; hexane; toluene; 1.1: Metallation / 1.2: Carboxylation / 2.1: Iodination / 3.1: Arylation;

DOI:10.1021/jo9915224

Reference yield:

N,N-dimethyl 2-methoxycarbonyl-3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide (284663-29-2) → N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide (284663-63-4)

Guidance literature:

Multi-step reaction with 2 steps

1: 100 percent / CF₃CO₂Ag; I₂ / tetrahydrofuran / 2 h / -78 °C

2: 98 percent / Pd(PPh₃)4; Na₂SO₄ / methanol; toluene / 2 h / 90 - 100 °C

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; iodine; silver trifluoroacetate; sodium sulfate; In tetrahydrofuran; methanol; toluene; 1: Iodination / 2: Arylation;

DOI:10.1021/jo9915224

upstream raw materials:

4-methoxyphenylboronic acid

N,N-dimethyl 2-methoxycarbonyl-3-trimethylsilyl-4-iodo-1H-pyrrole-1-sulfonamide

N-N-dimethyl 3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide

N,N-dimethyl 2-methoxycarbonyl-3,4-bis(trimethylsilyl)-1H-pyrrole-1-sulfonamide

Downstream raw materials:

N,N-dimethyl 2-methoxycarbonyl-3,4-bis(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide

N,N-dimethyl 2-methoxycarbonyl-3-phenylethynyl-4-(p-methoxyphenyl)-1H-pyrrole-1-sulfonamide

methyl 3,4-bis(4-methoxyphenyl)-1-[2-(4-methoxyphenyl)-2-oxoethyl]-1H-pyrrole-2-carboxylate

3,4-bis(4-methoxyphenyl)-1H-pyrrole-2-carboxylic acid methyl ester