4,5-Dichloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 4,5-Dichloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 685513-95-5
• Molecular Formula: C₁₆H₂₄Cl₂N₂Si
• Molecular Weight: 343.371
• DSSTox Substance ID: DTXSID30460350
• Nikkaji Number: J2.021.425B
• Wikidata: Q82284370
• Mol file: 685513-95-5.mol

Synonyms:4,5-Dichloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine;685513-95-5;(4,5-dichloropyrrolo[2,3-b]pyridin-1-yl)-tri(propan-2-yl)silane;SCHEMBL12594299;DTXSID30460350;MFCD13176652;AKOS015850077;CS-0454924;4,5-Dichloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine, AldrichCPR

Chemical Property of 4,5-Dichloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 4
• Exact Mass: 342.1085807
• Heavy Atom Count: 21
• Complexity: 340

Purity/Quality:

98%min ^*data from raw suppliers

4,5-Dichloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine Aldrich ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C)[Si](C(C)C)(C(C)C)N1C=CC2=C(C(=CN=C21)Cl)Cl

Technology Process of 4,5-Dichloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine

There total 4 articles about 4,5-Dichloro-1-(triisopropylsilyl)-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: 88.0%

4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (651744-48-8) → 4,5-dichloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (685513-95-5)

Guidance literature:

4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine; With sec.-butyllithium; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.5h;

With hexachloroethane; In tetrahydrofuran; cyclohexane; at -78 ℃; for 0.416667h; Further stages.;

DOI:10.1016/j.tetlet.2004.01.122

Reference yield:

4-chloro-7-azaindole (55052-28-3) → 4,5-dichloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (685513-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran; hexane / 0.25 h / 0 °C

1.2: 93.5 percent / tetrahydrofuran; hexane / 18 h / 80 °C

2.1: sec-butyllithium / tetrahydrofuran; cyclohexane / 0.5 h / -78 °C

2.2: 88 percent / hexachloroethane / tetrahydrofuran; cyclohexane / 0.42 h / -78 °C

With sec.-butyllithium; sodium hydride; In tetrahydrofuran; hexane; cyclohexane;

DOI:10.1016/j.tetlet.2004.01.122

Reference yield:

triisopropylsilyl chloride (13154-24-0) + 4-chloro-7-azaindole (55052-28-3) → 4,5-dichloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (685513-95-5)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 0 - 20 °C

2.1: sec.-butyllithium / tetrahydrofuran / 0.5 h / -50 °C

2.2: 4 h / -50 °C

With sec.-butyllithium; sodium hydride; In tetrahydrofuran;

upstream raw materials:

4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine

triisopropylsilyl chloride

4-chloro-7-azaindole

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