4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indole

Base Information

• Chemical Name: 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indole
• CAS No.: 690632-17-8
• Molecular Formula: C23H38BNO2Si
• Molecular Weight: 399.457
• Hs Code.: 2933299090
• DSSTox Substance ID: DTXSID90383793
• Wikidata: Q82175587
• Mol file: 690632-17-8.mol

Synonyms:690632-17-8;4-(4,4,5,5-TETRAMETHYL-1,3,2-DIOXABOROLAN-2-YL)-1-(TRIISOPROPYLSILYL)-1H-INDOLE;tri(propan-2-yl)-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)indol-1-yl]silane;1-(Triisopropylsilyl)-1H-indole-4-boronic acid, pinacol ester;1-Tris(isopropylsilyl)-1H-indole-4-boronic acid, pinacol ester;SCHEMBL3928563;DTXSID90383793;NGMKDRPSWHSLIM-UHFFFAOYSA-N;MFCD05865142;AKOS025293746;AB22941;J-513436;1-(Triisopropylsilyl)-1H-indole-4-boronic acid,pinacol ester;1-(triisopropylsilyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-indole;4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole;4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tri(propan-2-yl)silyl]-1H-indole;4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1-[tris(propan-2-yl)silyl]-1H-indole

Chemical Property of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indole

Chemical Property:

• Vapor Pressure: 1.01E-07mmHg at 25°C
• Refractive Index: 1.505
• Boiling Point: 433.7 °C at 760 mmHg
• Flash Point: 216.1 °C
• PSA: 23.39000
• Density: 0.98 g/cm³
• LogP: 5.96410
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 399.2764862
• Heavy Atom Count: 28
• Complexity: 525

Purity/Quality:

98%min ^*data from raw suppliers

1-Tris(isopropylsilyl)-1H-indole-4-boronic acid, pinacol ester ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: B1(OC(C(O1)(C)C)(C)C)C2=C3C=CN(C3=CC=C2)[Si](C(C)C)(C(C)C)C(C)C

Technology Process of 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indole

There total 4 articles about 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-YL)-1-(triisopropylsilyl)-1H-indole 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:

triisopropylsilyl chloride (13154-24-0) + indole-4-boronic acid pinacol ester (388116-27-6) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-1-(triisopropylsilyl)-1H-indole (690632-17-8)

Guidance literature:

With sodium hydride; In tetrahydrofuran; at 0 - 5 ℃;

Reference yield:

4-bromo-1H-indole (52488-36-5) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-1-(triisopropylsilyl)-1H-indole (690632-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 4 h / 90 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 5 °C

2.2: 0 - 20 °C

With potassium acetate; sodium hydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; dimethyl sulfoxide;

Reference yield:

bis(pinacol)diborane (73183-34-3) → 4-(4,4,5,5-tetramethyl-1,3,2-dioxoborolan-2-yl)-1-(triisopropylsilyl)-1H-indole (690632-17-8)

Guidance literature:

Multi-step reaction with 2 steps

1.1: potassium acetate / dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂ / dimethyl sulfoxide / 4 h / 90 °C

2.1: sodium hydride / tetrahydrofuran / 0.5 h / 0 - 5 °C

2.2: 0 - 20 °C

With potassium acetate; sodium hydride; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; In tetrahydrofuran; dimethyl sulfoxide;

upstream raw materials:

triisopropylsilyl chloride

indole-4-boronic acid pinacol ester

4-bromo-1H-indole

bis(pinacol)diborane

Downstream raw materials:

[4-benzyloxy-6-(1-triisopropylsilanyl-1H-indol-4-yl)-pyrimidin-2-yl]-pyridin-3-yl-amine

N-(pyridin3-yl)-N-(3-(1-(triisopropylsilyl)-1H-indol-4-yl)phenyl)acetamide

[3-(4-methoxy-benzylooxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-(1-oxy-pyridin-3-yl)-amine

(6-benzyloxy-pyridin-3-yl)-[3-(4-methoxy-benzyloxy)-5-(1-triisopropylsilanyl-1H-indol-4-yl)-phenyl]-amine

Refernces

• 1、 -. "ANTI-CANCER AGENTS ANS USES THEREOF". Page/Page column 82. . Retrieved 2010/11/29.