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

Base Information

• Chemical Name: Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine-1-carboxylate
• CAS No.: 942070-47-5
• Molecular Formula: C18H25BN2O4
• Molecular Weight: 344.218
• Hs Code.: 2934999090
• European Community (EC) Number: 805-016-9
• DSSTox Substance ID: DTXSID30682297
• Nikkaji Number: J2.795.221F
• Wikidata: Q72448583
• Mol file: 942070-47-5.mol

Synonyms:942070-47-5;TERT-BUTYL 3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE-1-CARBOXYLATE;1-Boc-7-Azaindole-3-boronic acid pinacol ester;tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrrolo[2,3-b]pyridine-1-carboxylate;1-BOC-7-Azaindole-3-boronic acid, pinacol ester;tert-butyl 3-(tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate;MFCD12407268;(1-(TERT-BUTOXYCARBONYL)-1H-PYRROLO[2,3-B]PYRIDIN-3-YL)BORONIC ACID PINACOL ESTER;SCHEMBL3346641;DTXSID30682297;FWSVXYOMGFESAP-UHFFFAOYSA-N;AKOS015950278;PB15081;3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrrolo[2,3-b]pyridine-1-carboxylic acid tert-butyl ester;AS-33453;SY027881;AM20061632;CS-0048356;FT-0684728;1-Boc-7-azaindole-3-boronic acid,pinacol ester;A844871;J-524480;1-(tert-Butyloxycarbonyl)-3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolane-2-yl)-1H-pyrrolo[2,3-b]pyridine;2-Methyl-2-propanyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate;tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridin-1-carboxylate;1-Boc-7-azaindole-3-boronic Acid Pinacol Ester;TERT-BUTYL3-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1H-PYRROLO[2,3-B]PYRIDINE-1-CARBOXYLATE

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

Chemical Property:

• Melting Point: 115-117 °C
• Boiling Point: 460.9±48.0 °C(Predicted)
• PKA: 2.68±0.30(Predicted)
• PSA: 62.58000
• Density: 1.13±0.1 g/cm3(Predicted)
• LogP: 3.11870
• Storage Temp.: Inert atmosphere,Store in freezer, under -20°C
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 3
• Exact Mass: 344.1907374
• Heavy Atom Count: 25
• Complexity: 516

Purity/Quality:

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

1-BOC-7-Azaindole-3-boronicacid,pinacolester ^*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=CN(C3=C2C=CC=N3)C(=O)OC(C)(C)C

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

There total 10 articles about Tert-butyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-YL)-1H-pyrrolo[2,3-B]pyridine-1-carboxylate 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: 93.0%

bis(pinacol)diborane (73183-34-3) + tert-butyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (226085-17-2) → 2-methyl-2-propanyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (942070-47-5)

Guidance literature:

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80 ℃; for 16h;

Reference yield: 85.0%

tert-butyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (192189-18-7) + 4,4,5,5-tetramethyl-[1,3,2]-dioxaboralane (25015-63-8) → 2-methyl-2-propanyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (942070-47-5)

Guidance literature:

With tetrakis(triphenylphosphine) palladium⁽⁰⁾; triethylamine; In 1,4-dioxane; at 80 ℃; for 3h; Inert atmosphere;

DOI:10.1039/c1ob05310h

Reference yield: 70.0%

1-(tert-butoxycarbonyl)-1H-pyrrolo<2,3-b>pyridine (138343-77-8) + bis(pinacol)diborane (73183-34-3) → 2-methyl-2-propanyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (942070-47-5)

Guidance literature:

With (1,5-cyclooctadiene)(methoxy)iridium(I) dimer; 3,4,7,8-Tetramethyl-o-phenanthrolin; In tetrahydrofuran; at 80 ℃; for 19h; Inert atmosphere; Glovebox;

DOI:10.1021/ja412563e

upstream raw materials:

bis(pinacol)diborane

tert-butyl 3-iodo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

tert-butyl 3-bromo-1H-pyrrolo[2,3-b]pyridine-1-carboxylate

1-(tert-butoxycarbonyl)-1H-pyrrolo<2,3-b>pyridine

Downstream raw materials:

4-(1H-pyrrolo[2,3-b]pyridin-3-yl)phenol

2-(1H-pyrrolo[2,3-b]pyridin-3-yl)benzenamine

Meriolin 1

3-(1-benzyl-1H-pyrazole-4-yl)-1H-pyrrolo[2,3-b]pyridine

Refernces

• 1、 Yuan, Kai,Kuang, Wenbin,Chen, Weijiao,Ji, Minghui,Min, Wenjian,Zhu, Yasheng,Hou, Yi,Wang, Xiao,Li, Jiaxing,Wang, Liping,Yang, Peng. "Discovery of novel and orally bioavailable CDK 4/6 inhibitors with high kinome selectivity, low toxicity and long-acting stability for the treatment of multiple myeloma". supporting information. . Retrieved 2021/12/09.
• 2、 -. "Five-membered heterocyclic oxo carboxylic acid compound and medical application thereof". Paragraph 0655-0659. . Retrieved 2021/05/01.