dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate

Base Information

• Chemical Name: dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate
• CAS No.: 1346685-05-9
• Molecular Formula: C₂₂H₁₅F₃N₂O₉S₃
• Molecular Weight: 604.562

Synonyms:dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate

Chemical Property of dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate

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Technology Process of dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate

There total 3 articles about dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate 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: 6.0%

1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo-[2,3-b]pyridine (942919-24-6) + dimethyl 3-bromo-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate (1346684-95-4) → dimethyl 3-bromo-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,5-thiophenedicarboxylate (1346685-04-8) + dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate (1346685-05-9)

Guidance literature:

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; water; at 70 ℃; chemoselective reaction; Sealed vessel;

DOI:10.1016/j.tetlet.2011.09.026

Reference yield:

4,5-dibromo-3-hydroxythiophene-2-carboxylic acid methyl ester (96232-71-2) → dimethyl 3-bromo-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,5-thiophenedicarboxylate (1346685-04-8) + dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate (1346685-05-9)

Guidance literature:

Multi-step reaction with 3 steps

1.1: n-butyllithium / 0.5 h / -78 °C

1.2: 2 h / -78 °C

2.1: pyridine / dichloromethane / 1 h / 0 - 20 °C

3.1: bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 70 °C / Sealed vessel

With pyridine; n-butyllithium; bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; dichloromethane; water; 3.1: Suzuki-Miyaura coupling;

DOI:10.1016/j.tetlet.2011.09.026

Reference yield:

dimethyl 3-bromo-4-hydroxy-2,5-thiophenedicarboxylate (1357482-07-5) → dimethyl 3-bromo-4-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-2,5-thiophenedicarboxylate (1346685-04-8) + dimethyl 3-[1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridin-4-yl]-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate (1346685-05-9)

Guidance literature:

Multi-step reaction with 2 steps

1: pyridine / dichloromethane / 1 h / 0 - 20 °C

2: bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate / 1,4-dioxane; water / 70 °C / Sealed vessel

With pyridine; bis(tri-t-butylphosphine)palladium⁽⁰⁾; potassium carbonate; In 1,4-dioxane; dichloromethane; water; 2: Suzuki-Miyaura coupling;

DOI:10.1016/j.tetlet.2011.09.026

upstream raw materials:

1-(phenylsulfonyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo-[2,3-b]pyridine

dimethyl 3-bromo-4-([(trifluoromethyl)sulfonyl]oxy)-2,5-thiophenedicarboxylate

dimethyl 3-bromo-4-hydroxy-2,5-thiophenedicarboxylate

4,5-dibromo-3-hydroxythiophene-2-carboxylic acid methyl ester

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