1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-1-[tris(1-methylethyl)silyl]-, methyl ester

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-1-[tris(1-methylethyl)silyl]-, methyl ester
• CAS No.: 685513-97-7
• Molecular Formula: C₁₈H₂₇ClN₂O₂Si
• Molecular Weight: 366.963
• Mol file: 685513-97-7.mol

Synonyms:1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-1-[tris(1-methylethyl)silyl]-, methyl ester

Chemical Property of 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-1-[tris(1-methylethyl)silyl]-, methyl ester

Chemical Property:

• Vapor Pressure: 1.03E-05mmHg at 25°C
• Refractive Index: 1.536
• Boiling Point: 371.4°C at 760 mmHg
• PKA: 2.98±0.30(Predicted)
• Flash Point: 178.4°C
• PSA: 44.12000
• Density: 1.12g/cm³
• LogP: 5.49990

Purity/Quality:

99%, ^*data from raw suppliers

Methyl4-chloro-1-(triisopropylsilanyl)-7-azaindole-5-carboxylate 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-1-[tris(1-methylethyl)silyl]-, methyl ester

There total 5 articles about 1H-Pyrrolo[2,3-b]pyridine-5-carboxylic acid, 4-chloro-1-[tris(1-methylethyl)silyl]-, methyl ester 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: 100.0%

methyl chloroformate (79-22-1) + 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine (651744-48-8) → 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (685513-97-7)

Guidance literature:

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

methyl chloroformate; In tetrahydrofuran; at -78 ℃; for 0.5h;

Reference yield:

4-chloro-7-azaindole (55052-28-3) → 4-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (685513-97-7)

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: 84 percent / 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-chloro-1-triisopropylsilanyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester (685513-97-7)

Guidance literature:

Multi-step reaction with 2 steps

1.1: sodium hydride / tetrahydrofuran / 1 h / 0 - 20 °C

1.2: 20 °C

2.1: sec.-butyllithium / tetrahydrofuran / 0.5 h / -78 °C / Inert atmosphere

2.2: 0.5 h / -78 °C

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

upstream raw materials:

methyl chloroformate

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

triisopropylsilyl chloride

4-chloro-7-azaindole

Downstream raw materials:

4-chloro-1H-pyrrolo[2,3-b]pyridine-5-carboxylic acid methyl ester

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