3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide

Base Information

Chemical Name:3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide
CAS No.:1445992-95-9
Molecular Formula:C₂₁H₁₇N₃O₃
Molecular Weight:359.384
Hs Code.:

Synonyms:3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide

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Chemical Property of 3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide

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Technology Process of 3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide

There total 8 articles about 3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide 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: 76.0%

: 1445993-93-0
3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzoyl chloride

: 1445992-95-9
3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide

Guidance literature:: With ammonium hydroxide; In tetrahydrofuran; at 20 ℃; for 2h; Inert atmosphere;
DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

: 884495-14-1
5-bromo-2-methoxy-4-methyl-3-nitropyridine

: 1445992-95-9
3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide

Guidance literature:: Multi-step reaction with 10 steps

1.1: lithium methanolate / N,N-dimethyl-formamide / 100 °C / Inert atmosphere

1.2: 16 h / 95 °C / Inert atmosphere

2.1: Ra-Ni 2800 / water; ethyl acetate / 0.5 h / 20 °C / 1551.49 Torr / Inert atmosphere

3.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.17 h / 20 °C / Inert atmosphere

3.2: 16 h / 20 °C / Inert atmosphere

4.1: hydrogenchloride / 1,4-dioxane / 16 h / 40 °C / Inert atmosphere

5.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / Inert atmosphere

5.2: 3 h / 20 °C / Inert atmosphere

6.1: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / ethanol; water; toluene / 24 h / 90 °C / Inert atmosphere

7.1: caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C / Inert atmosphere

8.1: sodium hydroxide / water; 1,4-dioxane / 2 h / 60 °C / Inert atmosphere

9.1: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 20 °C / Inert atmosphere

10.1: ammonium hydroxide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With hydrogenchloride; ammonium hydroxide; tetrakis(triphenylphosphine) palladium⁽⁰⁾; oxalyl dichloride; lithium methanolate; sodium hydride; sodium carbonate; caesium carbonate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide; toluene; mineral oil; 6.1: |Suzuki-Miyaura Coupling;
DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

: 1445993-92-9
ethyl 4-fluoro-3-(6-methyl-7-oxo-1-tosyl-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)benzoate

: 1445992-95-9
3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-phenoxybenzamide

Guidance literature:: Multi-step reaction with 4 steps

1: caesium carbonate / dimethyl sulfoxide / 12 h / 110 °C / Inert atmosphere

2: sodium hydroxide / water; 1,4-dioxane / 2 h / 60 °C / Inert atmosphere

3: oxalyl dichloride / N,N-dimethyl-formamide; dichloromethane / 2 h / 20 °C / Inert atmosphere

4: ammonium hydroxide / tetrahydrofuran / 2 h / 20 °C / Inert atmosphere

With ammonium hydroxide; oxalyl dichloride; caesium carbonate; sodium hydroxide; In tetrahydrofuran; 1,4-dioxane; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.1021/acs.jmedchem.7b00746