tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate

Base Information

• Chemical Name: tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate
• CAS No.: 1312812-82-0
• Molecular Formula: C₂₇H₃₄N₄O₃
• Molecular Weight: 462.592

Synonyms:tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate

Chemical Property of tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate

Chemical Property:

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Technology Process of tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate

There total 6 articles about tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate 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:

6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid (1261476-04-3) + trans-((4-aminomethyl)cyclohexylmethyl)carbamic acid tert-butyl ester (166168-16-7) → tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate (1312812-82-0)

Guidance literature:

With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; In dichloromethane; at 20 ℃; for 15h; Inert atmosphere;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid (479553-01-0) → tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate (1312812-82-0)

Guidance literature:

Multi-step reaction with 6 steps

1.1: methanol; hexane; dichloromethane / 0.5 h / 20 °C / Inert atmosphere

2.1: 3-chloro-benzenecarboperoxoic acid / 1,2-dimethoxyethane / 22.5 h / 20 °C / Inert atmosphere

3.1: chloroformic acid ethyl ester; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

4.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; toluene / 24 h / 80 °C / Inert atmosphere

5.1: lithium hydroxide / 1,4-dioxane / 1.5 h / 50 °C / Inert atmosphere

5.2: Inert atmosphere

6.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; chloroformic acid ethyl ester; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; 1,2-dimethoxyethane; hexane; dichloromethane; toluene; 4.1: Suzuki coupling;

DOI:10.1016/j.bmc.2011.04.014

Reference yield:

4-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide (1201748-37-9) → tert-butyl [(trans-4-((6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxamido)methyl)cyclohexyl)methyl]carbamate (1312812-82-0)

Guidance literature:

Multi-step reaction with 4 steps

1.1: chloroformic acid ethyl ester; 1,1,1,3,3,3-hexamethyl-disilazane / tetrahydrofuran / 16 h / 50 °C / Inert atmosphere

2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate / methanol; toluene / 24 h / 80 °C / Inert atmosphere

3.1: lithium hydroxide / 1,4-dioxane / 1.5 h / 50 °C / Inert atmosphere

3.2: Inert atmosphere

4.1: O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine / dichloromethane / 15 h / 20 °C / Inert atmosphere

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; chloroformic acid ethyl ester; potassium carbonate; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; triethylamine; 1,1,1,3,3,3-hexamethyl-disilazane; lithium hydroxide; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; toluene; 2.1: Suzuki coupling;

DOI:10.1016/j.bmc.2011.04.014

upstream raw materials:

1H-pyrrolo[2,3-b]pyridine-4-carboxylic acid

4-(methoxycarbonyl)-1H-pyrrolo[2,3-b]pyridine 7-oxide

methyl 6-chloro-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

methyl 6-phenyl-1H-pyrrolo[2,3-b]pyridine-4-carboxylate

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