N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

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Chemical Name:N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide
CAS No.:1374507-99-9
Molecular Formula:C₂₀H₂₃N₃O₃
Molecular Weight:353.421
Hs Code.:

Synonyms:N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

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Chemical Property of N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

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Technology Process of N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

There total 5 articles about N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide 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: 95.0%

: 1374507-94-4
N,N-diethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

: 123-11-5
4-methoxy-benzaldehyde

: 1374507-99-9
N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

Guidance literature:: N,N-diethyl-1H-pyrrolo[2,3-b]pyridine-3-carboxamide; With N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 - -40 ℃; for 0.666667h; Inert atmosphere;

4-methoxy-benzaldehyde; In tetrahydrofuran; cyclohexane; at -78 ℃; for 1h; Inert atmosphere;

With water; ammonium chloride; In tetrahydrofuran; cyclohexane; at 20 ℃; regioselective reaction; Inert atmosphere;
DOI:10.1002/anie.201108016

Reference yield:

: 271-63-6
7-Azaindole

: 1374507-99-9
N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

Guidance literature:: Multi-step reaction with 5 steps

1.1: potassium hydroxide / N,N-dimethyl-formamide / 0.17 h / 20 °C / Inert atmosphere

1.2: 0.5 h / 20 °C / Inert atmosphere

2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.5 h / 0 - 20 °C / Inert atmosphere

2.2: 20 °C / Inert atmosphere

3.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

5.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.67 h / -78 - -40 °C / Inert atmosphere

5.2: 1 h / -78 °C / Inert atmosphere

5.3: 20 °C / Inert atmosphere

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sec.-butyllithium; sodium hydride; potassium hydroxide; In tetrahydrofuran; hexane; cyclohexane; N,N-dimethyl-formamide; mineral oil;
DOI:10.1002/anie.201108016

Reference yield:

: 913983-25-2
3-iodo-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

: 1374507-99-9
N,N-diethyl-4-(hydroxy(4-methoxyphenyl)methyl)-1H-pyrrolo[2,3-b]pyridine-3-carboxamide

Guidance literature:: Multi-step reaction with 3 steps

1.1: n-butyllithium / tetrahydrofuran; hexane / 1 h / -78 °C / Inert atmosphere

1.2: 2 h / -78 °C / Inert atmosphere

2.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

3.1: N,N,N,N,-tetramethylethylenediamine; sec.-butyllithium / tetrahydrofuran; cyclohexane / 0.67 h / -78 - -40 °C / Inert atmosphere

3.2: 1 h / -78 °C / Inert atmosphere

3.3: 20 °C / Inert atmosphere

With n-butyllithium; N,N,N,N,-tetramethylethylenediamine; tetrabutyl ammonium fluoride; sec.-butyllithium; In tetrahydrofuran; hexane; cyclohexane;
DOI:10.1002/anie.201108016