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

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-
• CAS No.: 942919-26-8
• Molecular Formula: C13H17BN2O2
• Molecular Weight: 244.101
• Hs Code.: 29339900
• Mol file: 942919-26-8.mol

Synonyms:4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine;1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-;

Chemical Property of 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

Chemical Property:

• Vapor Pressure: 2.01E-06mmHg at 25°C
• Refractive Index: 1.563
• Boiling Point: 405.7 °C at 760 mmHg
• PKA: 13.71±0.40(Predicted)
• Flash Point: 199.2 °C
• PSA: 47.14000
• Density: 1.15 g/cm³
• LogP: 1.86210
• Storage Temp.: Sealed in dry,Store in freezer, under -20°C

Purity/Quality:

98%,99%, ^*data from raw suppliers

4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 25
• Safety Statements: 45-24/25

MSDS Files:

SDS file from LookChem

Useful:

• Uses: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine is used in organic synthesis, in particular, that of novel potent and selective Tetrahydropyrazolo[1,5-a]pyrazines as ATR inhibitors.

Technology Process of 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-

There total 2 articles about 1H-Pyrrolo[2,3-b]pyridine, 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)- 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: 94.0%

bis(pinacol)diborane (73183-34-3) + 4-chloro-7-azaindole (55052-28-3) → 4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (942919-26-8)

Guidance literature:

With potassium acetate; palladium diacetate; CyJohnPhos; In 1,4-dioxane; at 100 ℃; for 5h;

Reference yield:

bis(pinacol)diborane (73183-34-3) + 4-bromo-7-azaindole (348640-06-2) → 7-Azaindole (271-63-6) + 4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (942919-26-8)

Guidance literature:

With potassium acetate; palladium diacetate; 2,2'-bis-(diphenylphosphino)-1,1'-binaphthyl; In tetrahydrofuran; at 90 ℃; for 22h; Reagent/catalyst; Inert atmosphere; Glovebox;

DOI:10.1021/acs.oprd.0c00482

Reference yield: 83.0%

4-(4,4,5,5- tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (942919-26-8) + C28H40ClN5O5 → C35H45N7O5

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate; In 1,4-dioxane; water; at 95 ℃; Inert atmosphere;

upstream raw materials:

bis(pinacol)diborane

4-chloro-7-azaindole

4-bromo-7-azaindole

Downstream raw materials:

N-phenyl-N'-{4-[4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1-(2,2,2-trifluoroethyl)-1H-pyrazol-3-yl]phenyl}urea

tert-butyl 4-(4-(4-(ethoxycarbonyl)-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)oxazol-5-yl)phenyl)piperazine-1-carboxylate

N-{4-[1-ethyl-4-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1H-pyrazol-5-yl]phenyl}-N'-phenylurea

3-chloro-5-((1-((4-methoxy-2-(1H-pyrrolo[2,3-b]pyridin-4-yl)pyrimidin-5-yl)methyl)-6-oxo-4-(trifluoromethyl)-1,6-dihydropyrimidin-5-yl)oxy)benzonitrile

Refernces

• 1、 -. "THIENOPYRIMIDINE AS CDC7 KINASE INHIBITORS". Page/Page column 186. . Retrieved 2010/09/18.
• 2、 -. "OXAZOLE TYROSINE KINASE INHIBITORS". Page/Page column 137. . Retrieved 2009/01/20.