3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione

Base Information

• Chemical Name: 3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione
• CAS No.: 626604-30-6
• Molecular Formula: C₂₁H₂₀N₄O₃
• Molecular Weight: 376.415
• Mol file: 626604-30-6.mol

Synonyms:3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione

Chemical Property of 3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione

There total 4 articles about 3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-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: 84.0%

(3-{3-[4-(2-methoxy-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridin-1-yl}-propyl)-carbamic acid tert-butyl ester (626604-26-0) → 3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione (626604-30-6)

Guidance literature:

With trifluoroacetic acid; In dichloromethane;

DOI:10.1016/j.bmcl.2004.03.090

Reference yield:

7-Azaindole (271-63-6) → 3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione (626604-30-6)

Guidance literature:

Multi-step reaction with 4 steps

1.1: EtMgBr / tetrahydrofuran / -65 °C

1.2: 24 percent / tetrahydrofuran / -78 °C

2.1: 65 percent / Cs₂CO₃ / dimethylformamide / 68 °C

3.1: t-BuOK / tetrahydrofuran / 0 °C

3.2: 43 percent / aq. HCl

4.1: 84 percent / TFA / CH₂Cl₂

With ethylmagnesium bromide; potassium tert-butylate; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.03.090

Reference yield:

methyl α-oxo-1H-pyrrolo[2,3-b]pyridine-3-acetate (357263-49-1) → 3-[1-(3-aminopropyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-4-(2-methoxyphenyl)-1H-pyrrole-2,5-dione (626604-30-6)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 65 percent / Cs₂CO₃ / dimethylformamide / 68 °C

2.1: t-BuOK / tetrahydrofuran / 0 °C

2.2: 43 percent / aq. HCl

3.1: 84 percent / TFA / CH₂Cl₂

With potassium tert-butylate; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1016/j.bmcl.2004.03.090

upstream raw materials:

(3-{3-[4-(2-methoxy-phenyl)-2,5-dioxo-2,5-dihydro-1H-pyrrol-3-yl]-pyrrolo[2,3-b]pyridin-1-yl}-propyl)-carbamic acid tert-butyl ester

7-Azaindole

methyl α-oxo-1H-pyrrolo[2,3-b]pyridine-3-acetate

[1-(3-tert-butoxycarbonylamino-propyl)-1H-pyrrolo[2,3-b]pyridin-3-yl]-oxo-acetic acid methyl ester

Downstream raw materials:

N-[3-[3-[2,5-dihydro-4-(2-methoxyphenyl)-2,5-dioxo-1H-pyrrol-3-yl]-1H-pyrrolo[2,3-b]pyridin-1-yl]propyl]-acetamide