tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate

Base Information

• Chemical Name: tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate
• CAS No.: 882033-69-4
• Molecular Formula: C₂₈H₂₆ClFN₄O₆S
• Molecular Weight: 601.055
• Mol file: 882033-69-4.mol

Synonyms:

Chemical Property of tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate

Chemical Property:

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate

There total 10 articles about tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate 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:

4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (882033-67-2) + t-Butyl 3-bromo-5,6-dimethoxy-pyrrolo[3,2-b]pyridine-1-carboxylate (882033-35-4) → tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate (882033-69-4)

Guidance literature:

4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine; With n-butyllithium; tributyltin chloride; In tetrahydrofuran; at -75 ℃;

t-Butyl 3-bromo-5,6-dimethoxy-pyrrolo[3,2-b]pyridine-1-carboxylate; With copper(l) iodide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In toluene; Reflux;

DOI:10.1111/j.1747-0285.2010.00991.x

Reference yield:

3-bromo-5,6-dimethoxy-1H-pyrrolo[3,2-b]pyridine (882033-34-3) → tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate (882033-69-4)

Guidance literature:

Multi-step reaction with 2 steps

1.1: dmap; triethylamine / N,N-dimethyl-formamide

2.1: n-butyllithium; tributyltin chloride / tetrahydrofuran / -75 °C

2.2: Reflux

With dmap; n-butyllithium; tributyltin chloride; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; 2.2: Stille coupling;

DOI:10.1111/j.1747-0285.2010.00991.x

Reference yield:

C9H9N3O6 (882033-32-1) → tert-butyl 3-[4-chloro-5-fluoro-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridin-2-yl]-5,6-dimethoxypyrrolo[3,2-b]pyridine-1-carboxylate (882033-69-4)

Guidance literature:

Multi-step reaction with 4 steps

1.1: silica gel; iron; acetic acid / toluene / Reflux

2.1: bromine / N,N-dimethyl-formamide / -15 °C

3.1: dmap; triethylamine / N,N-dimethyl-formamide

4.1: n-butyllithium; tributyltin chloride / tetrahydrofuran / -75 °C

4.2: Reflux

With dmap; n-butyllithium; tributyltin chloride; bromine; silica gel; iron; acetic acid; triethylamine; In tetrahydrofuran; N,N-dimethyl-formamide; toluene; 4.2: Stille coupling;

DOI:10.1111/j.1747-0285.2010.00991.x

upstream raw materials:

4-chloro-5-fluoro-1H-pyrrolo[2,3-b]pyridine

p-toluenesulfonyl chloride

5,6-dimethoxypicolinaldehyde

1-(5,6-dimethoxy-3-nitropyridin-2-yl)-2-nitroethanol