4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Base Information

• Chemical Name: 4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one
• CAS No.: 1446235-30-8
• Molecular Formula: C₂₃H₂₀F₂N₂O₄S
• Molecular Weight: 458.486

Synonyms:4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Chemical Property of 4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

Chemical Property:

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Technology Process of 4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

There total 8 articles about 4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-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: 75.0%

4-(2-(2,4-difluorophenoxy)-5-(ethylsulfonylmethyl)phenyl)-6-methyl-1-tosyl-1H-pyrrolo[2,3-c]pyridin-7(6H)-one (1446236-33-4) → 4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (1446235-30-8)

Guidance literature:

With cetyltrimethylammonim bromide; potassium hydroxide; In tetrahydrofuran; water; at 100 ℃; for 44h; Inert atmosphere;

DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

3-bromo-4-(2,4-difluorophenoxy)benzaldehyde → 4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (1446235-30-8)

Guidance literature:

Multi-step reaction with 6 steps

1: sodium tetrahydroborate / ethanol; tetrahydrofuran / 1 h / 20 °C / Inert atmosphere

2: phosphorus tribromide / dichloromethane / 3 h / 20 °C / Inert atmosphere

3: N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

4: oxone / water; methanol / 1 h / 0 - 20 °C / Inert atmosphere

5: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; potassium phosphate / water; 1,4-dioxane / 1 h / 60 °C / Inert atmosphere

6: potassium hydroxide; cetyltrimethylammonim bromide / water; tetrahydrofuran / 44 h / 100 °C / Inert atmosphere

With sodium tetrahydroborate; potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; oxone; cetyltrimethylammonim bromide; phosphorus tribromide; potassium hydroxide; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In tetrahydrofuran; 1,4-dioxane; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 5: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.7b00746

Reference yield:

(3-bromo-4-(2,4-difluorophenoxy)phenyl)methanol → 4-{2-(2,4-difluorophenoxy)-5-[(ethylsulfonyl)methyl]phenyl}-6-methyl-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one (1446235-30-8)

Guidance literature:

Multi-step reaction with 5 steps

1: phosphorus tribromide / dichloromethane / 3 h / 20 °C / Inert atmosphere

2: N,N-dimethyl-formamide / 4 h / 20 °C / Inert atmosphere

3: oxone / water; methanol / 1 h / 0 - 20 °C / Inert atmosphere

4: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; potassium phosphate / water; 1,4-dioxane / 1 h / 60 °C / Inert atmosphere

5: potassium hydroxide; cetyltrimethylammonim bromide / water; tetrahydrofuran / 44 h / 100 °C / Inert atmosphere

With potassium phosphate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; oxone; cetyltrimethylammonim bromide; phosphorus tribromide; potassium hydroxide; 1,3,5,7-tetramethyl-8-phenyl-2,4,6-trioxa-8-phosphatricyclo[3.3.1.13,7]decane; In tetrahydrofuran; 1,4-dioxane; methanol; dichloromethane; water; N,N-dimethyl-formamide; 4: |Suzuki-Miyaura Coupling;

DOI:10.1021/acs.jmedchem.7b00746

upstream raw materials:

(3-bromo-4-(2,4-difluorophenoxy)benzyl)(ethyl)sulfane

6-methyl-1-[(4-methylphenyl)sulfonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,6-dihydro-7H-pyrrolo[2,3-c]pyridin-7-one

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

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

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