2-borono-5-methoxy-1H-Pyrrolo[3,2-b]pyridine-1-carboxylic acid 1-(1,1-dimethylethyl)ester

Base Information

• Chemical Name: 2-borono-5-methoxy-1H-Pyrrolo[3,2-b]pyridine-1-carboxylic acid 1-(1,1-dimethylethyl)ester
• CAS No.: 848357-95-9
• Molecular Formula: C13H17BN2O5
• Molecular Weight: 292.099
• Mol file: 848357-95-9.mol

Synonyms:5-methoxy-1H-indole-2-boronic acid 1-carboxylic acid tert-butyl ester;5-methoxypyrrolo[3,2-b]pyridine-2-boronic acid 1-carboxylic acid tert-butyl ester;

Chemical Property of 2-borono-5-methoxy-1H-Pyrrolo[3,2-b]pyridine-1-carboxylic acid 1-(1,1-dimethylethyl)ester

Chemical Property:

• PSA: 93.81000
• LogP: 0.50790

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 2-borono-5-methoxy-1H-Pyrrolo[3,2-b]pyridine-1-carboxylic acid 1-(1,1-dimethylethyl)ester

There total 4 articles about 2-borono-5-methoxy-1H-Pyrrolo[3,2-b]pyridine-1-carboxylic acid 1-(1,1-dimethylethyl)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: 37.0%

tert-butyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (357187-15-6) + Triisopropyl borate (5419-55-6) → (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid (848357-95-9)

Guidance literature:

tert-butyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate; With n-butyllithium; In tetrahydrofuran; at -78 ℃; for 1h;

Triisopropyl borate; In tetrahydrofuran; at -78 ℃; for 2h;

Reference yield: 37.0%

tert-butyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (357187-15-6) → (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid (848357-95-9)

Guidance literature:

tert-butyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate; With tert.-butyl lithium; In tetrahydrofuran; at -78 ℃; for 1h;

With Triisopropyl borate; In tetrahydrofuran; at -78 ℃; for 2h;

With hydrogenchloride; In water; pH=3 - 4;

Reference yield:

5-methoxy-4-aza-1H-indole (17288-40-3) → (1-(tert-butoxycarbonyl)-5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)boronic acid (848357-95-9)

Guidance literature:

Multi-step reaction with 2 steps

1.1: triethylamine; dmap / dichloromethane / 20 °C / Inert atmosphere

2.1: n-butyllithium / tetrahydrofuran / 1 h / -78 °C

2.2: 2 h / -78 °C

With dmap; n-butyllithium; triethylamine; In tetrahydrofuran; dichloromethane;

upstream raw materials:

tert-butyl 5-methoxy-1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Triisopropyl borate

5-methoxy-4-aza-1H-indole

di-tert-butyl dicarbonate

Downstream raw materials:

phenylphosphonic acid 3-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)-1H-indazol-5-yl ester methyl ester

2-(4-fluorophenyl)-5-(10-methoxy-6H-pyrido[2,3-c]pyrido[2',3':4,5]pyrrolo[1,2-c][1,3]oxazin-2-yl)-N-methyl-6-(N-methylmethylsulfonamido)benzofuran-3-carboxamide

phenylphosphonic acid ethyl ester 3-(5-methoxy-1H-pyrrolo[3,2-b]pyridin-2-yl)-1H-indazol-5-yl ester

Refernces

• 1、 -. "TETRACYCLIC HETEROCYCLE COMPOUNDS AND METHODS OF USE THEREOF FOR THE TREATMENT OF VIRAL DISEASES". Page/Page column 51; 52. . Retrieved 2013/03/26.