1-TOSYL-1H-PYRROLO[2,3-B]PYRIDINE-4-BORONIC ACID PINACOL ESTER

Base Information

• Chemical Name: 1-TOSYL-1H-PYRROLO[2,3-B]PYRIDINE-4-BORONIC ACID PINACOL ESTER
• CAS No.: 916176-50-6
• Molecular Formula: C20H23BN2O4S
• Molecular Weight: 398.291
• Hs Code.: 2933998090
• Mol file: 916176-50-6.mol

Synonyms:1-[(4-METHYLPHENYL)SULFONYL]-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE;1-TOSYL-1H-PYRROLO[2,3-B]PYRIDINE-4-BORONIC ACID PINACOL ESTER;1-PHENYLSULFONYL-4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-tosyl-1H-pyrrolo[2,3-b]pyridine;1H-Pyrrolo[2,3-b]pyridine, 1-[(4-Methylphenyl)sulfonyl]-4-(4,4,5,5-tetraMethyl-1,3,2-dioxaborolan-2-yl)-;1-[(4-Methylphenyl)sulfonyl]-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyr

Chemical Property of 1-TOSYL-1H-PYRROLO[2,3-B]PYRIDINE-4-BORONIC ACID PINACOL ESTER

Chemical Property:

• Boiling Point: 572.0±60.0 °C(Predicted)
• PKA: 0.22±0.30(Predicted)
• PSA: 78.80000
• Density: 1.24±0.1 g/cm3(Predicted)
• LogP: 3.96170
• Storage Temp.: 2-8°C

Purity/Quality:

99.3% ^*data from raw suppliers

1-Tosyl-1H-pyrrolo[2,3-b]pyridine-4-boronic acid, pinacol ester 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1-TOSYL-1H-PYRROLO[2,3-B]PYRIDINE-4-BORONIC ACID PINACOL ESTER

There total 9 articles about 1-TOSYL-1H-PYRROLO[2,3-B]PYRIDINE-4-BORONIC ACID PINACOL ESTER 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: 97.0%

4-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (348640-07-3) + bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (916176-50-6)

Guidance literature:

With potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In 1,2-dimethoxyethane; at 160 ℃; for 0.333333h; Product distribution / selectivity; microwave irradiatuon;

Reference yield: 78.2%

→ 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (916176-50-6)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 100 ℃; for 0.666667h; Inert atmosphere;

Reference yield:

4-bromo-7-azaindole (348640-06-2) → 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (916176-50-6)

Guidance literature:

Multi-step reaction with 2 steps

1: sodium hydroxide / tetra(n-butyl)ammonium hydrogensulfate / dichloromethane / 1 h / 20 °C

2: potassium acetate / (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 24 h / 90 °C / Inert atmosphere

With potassium acetate; sodium hydroxide; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; tetra(n-butyl)ammonium hydrogensulfate; In dichloromethane; N,N-dimethyl-formamide;

upstream raw materials:

4-bromo-1-(toluene-4-sulfonyl)-1H-pyrrolo[2,3-b]pyridine

bis(pinacol)diborane

1H-Pyrrolo[2,3-b]pyridine-7-oxide

7-Azaindole

Downstream raw materials:

4-[4-[1-[[S(R)]-S-methylsulfonimidoyl]cyclopropyl]-6-[(3R)-3-methyl-4-morpholinyl]-2-pyrimidinyl]-1H-pyrrolo[2,3-b]pyridine

4-{4-[(3R)-3-methylmorpholin-4-yl]-6-[1-((S)-S-methylsulfonimidoyl)cyclopropyl]pyrimidin-2-yl}-1H-pyrrolo[2,3-b]pyridine

(3R)-3-methyl-4-(6-(1-(S-methylsulfonimidoyl)cyclopropyl)-2-(1-tosyl-1H-pyrrolo[2,3-b]pyridine-4-yl)pyrimidin-4-yl)morpholine

(R)-3-methyl-4-(6-((R)-S-methylsulfonimidoylmethyl)-2-(1-tosyl-1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-4-yl)morpholine

Refernces

• 1、 -. "ATR INHIBITOR AND APPLICATION THEREOF". Paragraph 0105; 0107. . Retrieved 2020/12/29.
• 2、 -. "Azaquinazoline Inhibitors Of Atypical Protein Kinase C". Paragraph 0203. . Retrieved 2015/12/24.