3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine

Base Information

• Chemical Name: 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine
• CAS No.: 1111637-95-6
• Molecular Formula: C₁₄H₁₉BN₂O₂
• Molecular Weight: 258.128
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID201131189
• Mol file: 1111637-95-6.mol

Synonyms:1111637-95-6;3-METHYL-5-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE;3-METHYL-7-AZAINDOLE-5-BORONIC ACID PINACOL ESTER;3-methyl-5-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;(3-Methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)boronic acid pinacol ester;SCHEMBL2966812;VFFLHDCFYJJJEQ-UHFFFAOYSA-N;DTXSID201131189;MFCD12923386;AKOS015950103;PB28457;AS-33605;AM20050668;CS-0051252;A894772;1H-Pyrrolo[2,3-b]pyridine, 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property of 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine

Chemical Property:

• PKA: 14.18±0.40(Predicted)
• PSA: 47.14000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 2.17050
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 258.1539580
• Heavy Atom Count: 19
• Complexity: 345

Purity/Quality:

97% ^*data from raw suppliers

3-Methyl-7-azaindole-5-boronicAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=CC3=C(NC=C3C)N=C2

Technology Process of 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine

There total 8 articles about 3-Methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine 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: 58.0%

5-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine (1111637-94-5) + bis(pinacol)diborane (73183-34-3) → 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1111637-95-6)

Guidance literature:

With 1,1'-bis-(diphenylphosphino)ferrocene; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; potassium acetate; In 1,4-dioxane; at 100 ℃; Inert atmosphere;

Reference yield:

5-bromo-3-iodo-1-(4-methylbenzene-1-sulfonyl)-1H-pyrrolo[2,3-b]pyridine (875639-15-9) → 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1111637-95-6)

Guidance literature:

Multi-step reaction with 6 steps

1.1: isopropylmagnesium bromide / tetrahydrofuran / 0.5 h / 0 °C

1.2: 2 h / 20 °C

2.1: sodium tetrahydroborate; methanol / 0 - 20 °C

3.1: thionyl chloride / dichloromethane / 0.5 h / 0 - 20 °C

4.1: sodium tetrahydroborate / dimethyl sulfoxide / 2 h / 50 °C

5.1: sodium hydroxide; methanol / 2 h / Reflux

6.1: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 - 90 °C / Inert atmosphere

With methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; thionyl chloride; isopropylmagnesium bromide; potassium acetate; sodium hydroxide; In tetrahydrofuran; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

Reference yield:

5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde (1207626-51-4) → 3-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (1111637-95-6)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium tetrahydroborate; methanol / 0 - 20 °C

2: thionyl chloride / dichloromethane / 0.5 h / 0 - 20 °C

3: sodium tetrahydroborate / dimethyl sulfoxide / 2 h / 50 °C

4: sodium hydroxide; methanol / 2 h / Reflux

5: potassium acetate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / N,N-dimethyl-formamide / 80 - 90 °C / Inert atmosphere

With methanol; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium tetrahydroborate; thionyl chloride; potassium acetate; sodium hydroxide; In dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;

upstream raw materials:

5-bromo-3-methyl-1H-pyrrolo[2,3-b]pyridine

bis(pinacol)diborane

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

5-bromo-1-tosyl-1H-pyrrolo[2,3-b]pyridine-3-carbaldehyde