3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid

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Chemical Name:3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid
CAS No.:1446176-67-5
Molecular Formula:C₂₂H₁₅FN₄O₅
Molecular Weight:434.383
Hs Code.:

Synonyms:3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid

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Chemical Property of 3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid

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Technology Process of 3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid

There total 10 articles about 3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid 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: 85.0%

: 1446176-66-4
methyl 5-[3-{3-[(benzyloxy)carbonyl]phenyl}-4-carbamoyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-b]pyridin-6-yl]-2-fluorobenzoate

: 1446176-67-5
3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid

Guidance literature:: With sulfuric acid; at 20 ℃; for 0.5h;

Reference yield:

: 74439-45-5
ethyl 1-benzyl-6-hydroxy-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

: 1446176-67-5
3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid

Guidance literature:: Multi-step reaction with 10 steps

1: trichlorophosphate / N,N-dimethyl-formamide / 24 h / 0 - 80 °C / Inert atmosphere

2: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C

3: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

4: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

5: sulfuric acid / 1 h / 50 °C

6: sodium hydrogencarbonate; N-iodo-succinimide / 1,4-dioxane / 24 h / 20 °C

7: toluene-4-sulfonic acid / dichloromethane / 12 h / 20 °C

8: potassium carbonate; sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate hydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1 h / 95 °C / Inert atmosphere

9: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; ammonium bicarbonate / 2-methyltetrahydrofuran / 2 h / 20 °C / Inert atmosphere

10: sulfuric acid / 0.5 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-iodo-succinimide; sulfuric acid; sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate hydrate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; ammonium bicarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; triethylamine; sodium hydroxide; trichlorophosphate; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;

Reference yield:

: 1446176-52-8
ethyl 1-benzyl-6-chloro-1H-pyrazolo[3,4-b]pyridine-4-carboxylate

: 1446176-67-5
3-{4-carbamoyl-6-[4-fluoro-3-(methoxycarbonyl)phenyl]-1H-pyrazolo[3,4-b]pyridin-3-yl}benzoic acid

Guidance literature:: Multi-step reaction with 9 steps

1: sodium hydroxide / tetrahydrofuran / 2 h / 20 °C

2: potassium carbonate / N,N-dimethyl-formamide / 2 h / 20 °C

3: caesium carbonate / N,N-dimethyl-formamide / 2 h / 80 °C / Inert atmosphere

4: sulfuric acid / 1 h / 50 °C

5: sodium hydrogencarbonate; N-iodo-succinimide / 1,4-dioxane / 24 h / 20 °C

6: toluene-4-sulfonic acid / dichloromethane / 12 h / 20 °C

7: potassium carbonate; sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate hydrate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 1 h / 95 °C / Inert atmosphere

8: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; ammonium bicarbonate / 2-methyltetrahydrofuran / 2 h / 20 °C / Inert atmosphere

9: sulfuric acid / 0.5 h / 20 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; N-iodo-succinimide; sulfuric acid; sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1′-biphenyl-3-sulfonate hydrate; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; sodium hydrogencarbonate; ammonium bicarbonate; potassium carbonate; caesium carbonate; toluene-4-sulfonic acid; triethylamine; sodium hydroxide; In tetrahydrofuran; 2-methyltetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide;