1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

Base Information

• Chemical Name: 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-
• CAS No.: 869335-19-3
• Molecular Formula: C13H19ClN2OSi
• Molecular Weight: 282.845
• DSSTox Substance ID: DTXSID50470416
• Nikkaji Number: J2.293.602F
• Mol file: 869335-19-3.mol

Synonyms:869335-19-3;1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-;2-[(4-chloropyrrolo[2,3-b]pyridin-1-yl)methoxy]ethyl-trimethylsilane;4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1h-pyrrolo[2,3-b]pyridine;4-Chloro-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine;SCHEMBL352030;DTXSID50470416;XZIRRBIOVUGENX-UHFFFAOYSA-N;SB13962;F17921;4-chloro-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine;4-chloro-1-[2-(trimethylsily)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine;4-Chloro-1-[2-(trimethylsilyl)ethoxy]methyl-1H-pyrrolo[2,3-b]pyridine

Chemical Property of 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

Chemical Property:

• PSA: 27.05000
• LogP: 4.00200
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 282.0955175
• Heavy Atom Count: 18
• Complexity: 272

Purity/Quality:

97% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C[Si](C)(C)CCOCN1C=CC2=C(C=CN=C21)Cl

Technology Process of 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]-

There total 4 articles about 1H-Pyrrolo[2,3-b]pyridine, 4-chloro-1-[[2-(trimethylsilyl)ethoxy]methyl]- 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: 89.6%

(2-trimethylethylsilylethoxy)methyl chloride (76513-69-4) + 4-chloro-7-azaindole (55052-28-3) → 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (869335-19-3)

Guidance literature:

With sodium hydride; In N,N-dimethyl-formamide;

Reference yield:

4-chloro-2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine (1221714-47-1) → 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (869335-19-3)

Guidance literature:

With dicyclohexyl-(2',6'-dimethoxybiphenyl-2-yl)-phosphane; dihydroxyborane; palladium diacetate; caesium carbonate; In 1,4-dioxane; water; at 60 ℃; for 12h;

DOI:10.1021/jm3016014

Reference yield:

7-Azaindole (271-63-6) → 4-chloro-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridine (869335-19-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 3-chloro-benzenecarboperoxoic acid / ethyl acetate / 0 - 20 °C

2: methanesulfonyl chloride / N,N-dimethyl-formamide / 50 - 70 °C / Inert atmosphere

3: sodium hydride / N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere

With sodium hydride; methanesulfonyl chloride; 3-chloro-benzenecarboperoxoic acid; In ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/acs.jmedchem.7b00178

upstream raw materials:

(2-trimethylethylsilylethoxy)methyl chloride

4-chloro-7-azaindole

4-chloro-2-iodo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

7-Azaindole

Downstream raw materials:

N-(2-fluoro-4-nitrophenyl)-1-{[2-(trimethylsilyl)ethoxy]methyl}-1H-pyrrolo[2,3-b]pyridin-4-amine

4-chloro-2-phenyl-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridine

3-fluoro-4-[2-phenyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy]-phenyl-carbamic acid t-butyl ester

3-fluoro-4-(2-phenyl-1H-pyrrolo[2,3-b]pyridin-4-yloxy)-phenylamine