4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione

Base Information

• Chemical Name: 4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione
• CAS No.: 626605-11-6
• Molecular Formula: C₄₃H₅₄N₄O₃Si₂
• Molecular Weight: 731.098
• Mol file: 626605-11-6.mol

Synonyms:4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione

Chemical Property of 4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione

There total 6 articles about 4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione 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: 60.0%

3-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-4-chloro-pyrrole-2,5-dione (626605-09-2) + 1-(triisopropyl)pyrrole-3-boronic acid → 4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione (626605-11-6)

Guidance literature:

With potassium fluoride; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(tri-tert-butylphosphine)palladium⁽⁰⁾; at 23 ℃; for 18h;

Reference yield: 60.0%

3-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-4-chloro-pyrrole-2,5-dione (626605-09-2) + 1-(triisopropylsilyl)-1H-pyrrole-3-boronic acid (138900-55-7) → 4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione (626605-11-6)

Guidance literature:

With potassium fluoride; bis(tri-t-butylphosphine)palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; at 23 ℃; for 18h;

DOI:10.1016/j.bmc.2004.04.010

Reference yield:

2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-acetamide (626605-07-0) → 4-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-1'-triisopropylsilanyl-1'H-[3,3']bipyrrolyl-2,5-dione (626605-11-6)

Guidance literature:

Multi-step reaction with 3 steps

1: 80 percent / potassium tert-butoxide / tetrahydrofuran / 0.33 h

2: 73 percent / oxalyl chloride / CH₂Cl₂; dimethylformamide / 1 h / 23 °C

3: 60 percent / potassium fluoride / Pd₂(dba)3; Pd(P(t-Bu)3)2 / tetrahydrofuran / 18 h / 23 °C

With potassium fluoride; oxalyl dichloride; potassium tert-butylate; bis(tri-t-butylphosphine)palladium⁽⁰⁾; tris(dibenzylideneacetone)dipalladium ⁽⁰⁾; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; 3: Suzuki cross-coupling;

DOI:10.1016/j.bmc.2004.04.010

upstream raw materials:

3-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-4-chloro-pyrrole-2,5-dione

1-(triisopropylsilyl)-1H-pyrrole-3-boronic acid

2-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-acetamide

3-{1-[3-(tert-butyl-diphenyl-silanyloxy)-propyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}-4-hydroxy-pyrrole-2,5-dione