4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester
• CAS No.: 1175014-70-6
• Molecular Formula: C₃₀H₃₂N₄O₄
• Molecular Weight: 512.608

Synonyms:4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Chemical Property of 4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

Chemical Property:

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Technology Process of 4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester

There total 9 articles about 4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester 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: 58.0%

4-(2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester (1175014-69-3) + ortho-cresol (95-48-7,77504-84-8) → 4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (1175014-70-6)

Guidance literature:

With sodium hydride; In 1-methyl-pyrrolidin-2-one; at 20 - 140 ℃; Microwave irradiation;

DOI:10.1016/j.bmcl.2011.06.114

Reference yield:

1H-pyrrolo[3,2-b]pyridine (272-49-1) → 4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (1175014-70-6)

Guidance literature:

Multi-step reaction with 8 steps

1: 8-quinolinol; copper(l) iodide; potassium carbonate / dimethyl sulfoxide / 130 °C

2: bromine; tert-butyl alcohol / water / 20 °C

3: palladium on activated charcoal; hydrogen / ethanol / 20 °C

4: pyridine; trichlorophosphate / dichloromethane / 0 - 20 °C

5: trichlorophosphate / dichloromethane / 100 °C

6: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol / 20 °C

7: 4-methyl-morpholine; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C

8: sodium hydride / 1-methyl-pyrrolidin-2-one / 20 - 140 °C / Microwave irradiation

With 4-methyl-morpholine; pyridine; sodium chlorite; sodium dihydrogenphosphate; copper(l) iodide; 8-quinolinol; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; hydrogen; bromine; sodium hydride; potassium carbonate; tert-butyl alcohol; trichlorophosphate; In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; tert-butyl alcohol; 4: Vilsmeier-Haack reaction;

DOI:10.1016/j.bmcl.2011.06.114

Reference yield:

1-phenyl-1H-pyrrolo[3,2-b]pyridine (514182-79-7) → 4-[1-phenyl-2-(2-methyl-phenoxy)-1H-pyrrolo[3,2-b]pyridine-3-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (1175014-70-6)

Guidance literature:

Multi-step reaction with 7 steps

1: bromine; tert-butyl alcohol / water / 20 °C

2: palladium on activated charcoal; hydrogen / ethanol / 20 °C

3: pyridine; trichlorophosphate / dichloromethane / 0 - 20 °C

4: trichlorophosphate / dichloromethane / 100 °C

5: sodium dihydrogenphosphate; sodium chlorite / tert-butyl alcohol / 20 °C

6: 4-methyl-morpholine; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C

7: sodium hydride / 1-methyl-pyrrolidin-2-one / 20 - 140 °C / Microwave irradiation

With 4-methyl-morpholine; pyridine; sodium chlorite; sodium dihydrogenphosphate; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; palladium on activated charcoal; hydrogen; bromine; sodium hydride; tert-butyl alcohol; trichlorophosphate; In 1-methyl-pyrrolidin-2-one; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol; 3: Vilsmeier-Haack reaction;

DOI:10.1016/j.bmcl.2011.06.114

upstream raw materials:

4-(2-chloro-1-phenyl-1H-pyrrolo[3,2-b]pyridine-3-carbonyl)-piperazine-1-carboxylic acid tert-butyl ester

ortho-cresol

1H-pyrrolo[3,2-b]pyridine

1-phenyl-1H-pyrrolo[3,2-b]pyridine

Downstream raw materials:

C₂₅H₂₄N₄O₂

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