6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Base Information

• Chemical Name: 6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one
• CAS No.: 1445993-94-1
• Molecular Formula: C₁₉H₁₉N₃O₅
• Molecular Weight: 369.377

Synonyms:6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Chemical Property of 6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

Chemical Property:

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Technology Process of 6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

There total 5 articles about 6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one 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: 66.0%

Tetrahydro-pyran-4-ol (2081-44-9) + 4-(2-fluoro-5-nitrophenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]-pyridin-7(6H)-one (1445993-88-3) → 6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (1445993-94-1)

Guidance literature:

Tetrahydro-pyran-4-ol; With sodium hydride; In tetrahydrofuran; mineral oil; at 20 ℃; for 0.166667h; Inert atmosphere;

4-(2-fluoro-5-nitrophenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]-pyridin-7(6H)-one; In tetrahydrofuran; mineral oil; at 50 ℃; for 2h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

5-bromo-2-methoxy-4-methyl-3-nitropyridine (884495-14-1) → 6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (1445993-94-1)

Guidance literature:

Multi-step reaction with 7 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: sodium carbonate / 1,2-dimethoxyethane; water / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube

7.1: sodium hydride / mineral oil; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

7.2: 2 h / 50 °C / Inert atmosphere

With hydrogenchloride; lithium methanolate; sodium hydride; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; water; ethyl acetate; N,N-dimethyl-formamide; mineral oil; 6.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

4-bromo-7-methoxy-1-(4-methylbenzenesulfonyl)pyrrolo[2,3-c]pyridine (1445993-85-0) → 6-methyl-4-(5-nitro-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (1445993-94-1)

Guidance literature:

Multi-step reaction with 4 steps

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

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

2.2: 3 h / 20 °C / Inert atmosphere

3.1: sodium carbonate / 1,2-dimethoxyethane; water / 0.5 h / 120 °C / Microwave irradiation; Inert atmosphere; Sealed tube

4.1: sodium hydride / mineral oil; tetrahydrofuran / 0.17 h / 20 °C / Inert atmosphere

4.2: 2 h / 50 °C / Inert atmosphere

With hydrogenchloride; sodium hydride; sodium carbonate; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; water; N,N-dimethyl-formamide; mineral oil; 3.1: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.7b00746

upstream raw materials:

4-bromo-6-methyl-1-[(4-methylphenyl)sulfonyl]-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Tetrahydro-pyran-4-ol

4-(2-fluoro-5-nitrophenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]-pyridin-7(6H)-one

5-bromo-2-methoxy-4-methyl-3-nitropyridine

Downstream raw materials:

N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]propane-1-sulfonamide

2,2,2-trifluoro-N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]ethanesulfonamide

4-(5-amino-2-(tetrahydro-2H-pyran-4-yloxy)phenyl)-6-methyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one

N-[3-(6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-4-yl)-4-(tetrahydro-2H-pyran-4-yloxy)phenyl]methanesulfonamide

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