5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 1111638-02-8
• Molecular Formula: C8H7BrN2
• Molecular Weight: 211.061
• Hs Code.: 2933990090
• Mol file: 1111638-02-8.mol

Synonyms:1H-pyrrolo[2,3-b]pyridine, 5-bromo-2-methyl-;5-Bromo-2-methyl-7-azaindole;

Chemical Property of 5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• Boiling Point: 320.567 °C at 760 mmHg
• PKA: 13.49±0.40(Predicted)
• Flash Point: 147.674 °C
• PSA: 28.68000
• Density: 1.655 g/cm³
• LogP: 2.93000
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%,99%, ^*data from raw suppliers

5-Bromo-2-methyl-1h-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22-41

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 5-Bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine

There total 6 articles about 5-Bromo-2-methyl-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: 97.0%

5-bromo-3-(prop-1-yn-1-yl)pyridin-2-amine (1312755-43-3) → 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (1111638-02-8)

Guidance literature:

With potassium tert-butylate; In tert-butyl alcohol; at 85 ℃; for 1h;

Reference yield: 82.0%

5-bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine (1111638-01-7) → 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (1111638-02-8)

Guidance literature:

With tetrabutyl ammonium fluoride; In tetrahydrofuran; at 20 ℃; for 6h;

DOI:10.1021/acsmedchemlett.7b00157

Reference yield:

5-bromo-1H-pyrrolo[2,3-b]pyridine (183208-35-7) → 5-bromo-2-methyl-1H-pyrrolo[2,3-b]pyridine (1111638-02-8)

Guidance literature:

Multi-step reaction with 3 steps

1.1: sodium hydroxide; tetrabutylammomium bromide / dichloromethane / 2 h / 0 °C

2.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 0.5 h / -35 °C

2.2: 2 h / -35 - 20 °C

3.1: sodium hydroxide / methanol / 2 h / Reflux

With n-butyllithium; tetrabutylammomium bromide; diisopropylamine; sodium hydroxide; In tetrahydrofuran; methanol; hexane; dichloromethane;

upstream raw materials:

5-bromo-2-methyl-1-(phenylsulfonyl)-1H-pyrrolo[2,3-b]pyridine

2-amino-3-iodo-5-bromopyridine

5-bromo-2-pyridylamine

5-bromo-3-(prop-1-yn-1-yl)pyridin-2-amine

Downstream raw materials:

2-methyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine

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

9-benzenesulfonyl-5-hydroxy-9H-dipyrido[2,3-b:4',3'-d]pyrrole-6-carbonitrile

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

Refernces

• 1、 -. "COMPOUND FUNCTIONING AS BROMODOMAIN PROTEIN INHIBITOR, AND COMPOSITION". Paragraph 0108; 0111. . Retrieved 2020/11/22.
• 2、 -. "AZAINDOLES AS INHIBITORS OF HPK1". . . Retrieved 2018/10/19.