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1198605-53-6

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1198605-53-6 Usage

Description

Methyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate is a versatile chemical compound utilized as a reagent in organic synthesis. It features a pyrrole ring with a carboxylate group and a boron-containing group, known for its reactivity in cross-coupling reactions and functional group transformations. Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate serves as a building block for the synthesis of complex organic molecules and pharmaceuticals, and its boron-containing group is instrumental in developing new materials and understanding the reactivity of boron in organic chemistry.

Uses

Used in Organic Synthesis:
Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate is used as a reagent for organic synthesis, facilitating the formation of complex organic molecules and pharmaceuticals. Its unique structure allows for various chemical reactions, making it a valuable component in the synthesis process.
Used in Cross-Coupling Reactions:
In the field of organic chemistry, Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate is used as a reactant in cross-coupling reactions, enabling the formation of carbon-carbon bonds and contributing to the synthesis of diverse organic compounds.
Used in Functional Group Transformations:
Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate is also utilized as a reagent for functional group transformations, allowing chemists to modify the functional groups of organic molecules, which is crucial for the development of new pharmaceuticals and materials.
Used in the Development of New Materials:
Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate is used as a building block in the development of new materials, thanks to its boron-containing group, which offers unique properties and reactivity for material science applications.
Used in Pharmaceutical Synthesis:
In the pharmaceutical industry, Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate is used as a key intermediate in the synthesis of various drugs, contributing to the development of new medications and therapies.
Used in the Study of Boron Reactivity:
Methyl 4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate is used as a research tool for studying the reactivity of boron in organic chemistry, providing insights into the behavior of boron-containing compounds and their potential applications in various fields.

Check Digit Verification of cas no

The CAS Registry Mumber 1198605-53-6 includes 10 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 7 digits, 1,1,9,8,6,0 and 5 respectively; the second part has 2 digits, 5 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 1198605-53:
(9*1)+(8*1)+(7*9)+(6*8)+(5*6)+(4*0)+(3*5)+(2*5)+(1*3)=186
186 % 10 = 6
So 1198605-53-6 is a valid CAS Registry Number.

1198605-53-6Synthetic route

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
942070-38-4

4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)pyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
at 180℃; for 0.3h;99%
at 180℃; for 0.3h;76%
With zinc dibromide In acetonitrile at 50℃; for 4h;2.5 g
4-bromopyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester
156237-78-4

4-bromopyrrole-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
2: zinc dibromide / acetonitrile / 4 h / 50 °C
View Scheme
methyl 4-bromo-1H-pyrrole-2-carboxylate
934-05-4

methyl 4-bromo-1H-pyrrole-2-carboxylate

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine; dmap / dichloromethane / 3 h / 20 °C
2: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane / 3 h / 100 °C / Inert atmosphere
3: zinc dibromide / acetonitrile / 4 h / 50 °C
View Scheme
N-(2-chloro-5-bromopyridin-3-yl)benzenesulfonamide
1083326-17-3

N-(2-chloro-5-bromopyridin-3-yl)benzenesulfonamide

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

methyl 4-(6-chloro-5-(phenylsulfonamido)pyridin-3-yl)-1H-pyrrole-2-carboxylate

methyl 4-(6-chloro-5-(phenylsulfonamido)pyridin-3-yl)-1H-pyrrole-2-carboxylate

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); potassium acetate In 1,4-dioxane at 80℃; for 8h; Suzuki-Miyaura Coupling; Inert atmosphere;61%
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

1-[(3-bromopropoxy)methyl]-benzene
54314-84-0

1-[(3-bromopropoxy)methyl]-benzene

methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate
1380306-60-4

methyl 1-[3-(benzyloxy)propyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylate

Conditions
ConditionsYield
With caesium carbonate In N,N-dimethyl-formamide at 70℃; for 16h;46%
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

methyl 4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1-(3-hydroxypropyl)-1H-pyrrole-2-carboxylate
1380306-54-6

methyl 4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1-(3-hydroxypropyl)-1H-pyrrole-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C
2: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation
3: 5% Pd-CaCO3 / palladium 10% on activated carbon / ethanol / 16 h / 20 °C
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

methyl 1-[3-(benzyloxy)propyl]-4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1H-pyrrole-2-carboxylate
1380306-56-8

methyl 1-[3-(benzyloxy)propyl]-4-[5-({2-[(4-{[ethoxy(hydroxy)phosphoryl]methyl}-2-methoxyphenyl)amino]-5-(trifluoromethyl)pyrimidin-4-yl}amino)-6-(methylcarbamoyl)pyridin-2-yl]-1H-pyrrole-2-carboxylate

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: caesium carbonate / N,N-dimethyl-formamide / 16 h / 70 °C
2: potassium carbonate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2 / 1,4-dioxane; water / 0.5 h / 100 °C / Inert atmosphere; Microwave irradiation
View Scheme
4-bromo-2(1H)-pyridinone
36953-37-4

4-bromo-2(1H)-pyridinone

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water for 2h; Inert atmosphere; Reflux;110 mg
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-phenylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

4-(3-phenylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Reflux; Inert atmosphere
2.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol / 3 h / Reflux; Inert atmosphere
3.1: sodium hydroxide; water / ethanol / 4 h / Reflux
4.1: sodium hydrogencarbonate; HATU / N,N-dimethyl-formamide / 0.33 h / 20 °C
4.2: 2 h / 20 °C
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid

4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / Inert atmosphere; Reflux
2: sodium hydroxide; water / ethanol / 1 h / 80 °C
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

4-(2-hydroxypyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / 1,4-dioxane; water / 2 h / Inert atmosphere; Reflux
2.1: sodium hydroxide; water / ethanol / 1 h / 80 °C
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 3 h / 20 °C
3.2: 0.5 h / 20 °C
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-methylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid

4-(3-methylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Inert atmosphere; Reflux
2: sodium hydroxide; water / ethanol / 2 h / Reflux
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-methylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

4-(3-methylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Inert atmosphere; Reflux
2.1: sodium hydroxide; water / ethanol / 2 h / Reflux
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C
3.2: 20 °C
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-bromopyridin-4-yl)-1H-pyrrole-2-carboxylic acid

4-(3-bromopyridin-4-yl)-1H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Reflux; Inert atmosphere
2: sodium hydroxide; water / ethanol / 4 h / Reflux
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-bromopyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

4-(3-bromopyridin-4-yl)-1H-pyrrole-2-carboxylic acid amide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Reflux; Inert atmosphere
2.1: sodium hydroxide; water / ethanol / 4 h / Reflux
3.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / N,N-dimethyl-formamide / 0.5 h / 20 °C
3.2: 20 °C
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-phenylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-phenylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Reflux; Inert atmosphere
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol / 3 h / Reflux; Inert atmosphere
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-phenylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid

4-(3-phenylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol; water / 3 h / Reflux; Inert atmosphere
2: (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate / ethanol / 3 h / Reflux; Inert atmosphere
3: sodium hydroxide; water / ethanol / 4 h / Reflux
View Scheme
4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-bromo-3-methylpyridine
10168-00-0

4-bromo-3-methylpyridine

4-(3-methylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-methylpyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In ethanol; water for 3h; Inert atmosphere; Reflux;150 mg
dibromo-3,4 pyridine
13534-90-2

dibromo-3,4 pyridine

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester
1198605-53-6

4-(4,4,5,5-tetramethyl-[1,3,2]-dioxaborolan-2-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-bromopyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

4-(3-bromopyridin-4-yl)-1H-pyrrole-2-carboxylic acid methyl ester

Conditions
ConditionsYield
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate In ethanol; water for 3h; Reflux; Inert atmosphere;1 g

1198605-53-6Relevant articles and documents

NOVEL PYRROLE DERIVATIVES FOR THE TREATMENT OF CANCER

-

, (2014/10/15)

The invention provides a method for the treatment of cancer, which method comprises the general formula (I) wherein R1, R2, R3, R4 and W are as described herein.

Boc groups as protectors and directors for ir-catalyzed C-H borylation of heterocycles

Kallepalli, Venkata A.,Shi, Feng,Paul, Sulagna,Onyeozili, Edith N.,Maleczka Jr., Robert E.,Smith III, Milton R.

supporting information; experimental part, p. 9199 - 9201 (2010/03/02)

(Chemical Equation Presented) Ir-catalyzed C-H borylation is found to be compatible with Boc protecting groups. Thus, pyrroles, indoles, and azaindoles can be selectively functionalized at C-H positions β to N. The Boc group can be removed on thermolysis

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