(2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,2⁽⁶⁾-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate

Base Information

• Chemical Name: (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,2⁽⁶⁾-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate
• CAS No.: 1346675-49-7
• Molecular Formula: C₂₇H₃₃BFNO₅S
• Molecular Weight: 513.438

Synonyms:(2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,2⁽⁶⁾-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate

Chemical Property of (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,2⁽⁶⁾-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate

Chemical Property:

Purity/Quality:

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Technology Process of (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,2⁽⁶⁾-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate

There total 16 articles about (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,2⁽⁶⁾-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate 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%

(2-bromo-6-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-4-fluorophenyl)methyl acetate (1346675-48-6) + bis(pinacol)diborane (73183-34-3) → (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate (1346675-49-7)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 15h; Inert atmosphere;

Reference yield:

1,3-dibromo-5-fluoro-2-iodobenzene (62720-29-0) → (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate (1346675-49-7)

Guidance literature:

Multi-step reaction with 6 steps

1: hydrogenchloride / toluene; diethyl ether / 2 h / -35 - -25 °C

2: toluene; diethyl ether / 3 h / -25 - 10 °C

3: sodium tetrahydroborate / ethanol / 4 h / 10 °C

4: pyridine / dichloromethane / 5 h / 0 - 20 °C

5: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

6: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

With pyridine; hydrogenchloride; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; diethyl ether; ethanol; dichloromethane; toluene;

Reference yield:

2,6-dibromo-4-fluorobenzaldehyde (938467-02-8) → (2-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.02,6]dodeca-1(8),2(6)-dien-10-yl}-4-fluoro-6-(tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl)methyl acetate (1346675-49-7)

Guidance literature:

Multi-step reaction with 4 steps

1: sodium tetrahydroborate / ethanol / 4 h / 10 °C

2: pyridine / dichloromethane / 5 h / 0 - 20 °C

3: tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; caesium carbonate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

4: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate / 1,4-dioxane / 15 h / 100 °C / Inert atmosphere

With pyridine; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium acetate; caesium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1,4-dioxane; ethanol; dichloromethane;

upstream raw materials:

(2-bromo-6-{4,4-dimethyl-9-oxo-7-thia-10-azatricyclo[6.4.0.0^2,6]dodeca-1⁽⁸⁾,2⁽⁶⁾-dien-10-yl}-4-fluorophenyl)methyl acetate

bis(pinacol)diborane

1,3-dibromo-5-fluoro-2-iodobenzene

2,6-dibromo-4-fluorobenzaldehyde

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