6-bromo-1H-pyrrolo[2,3-b]pyridine

Base Information

• Chemical Name: 6-bromo-1H-pyrrolo[2,3-b]pyridine
• CAS No.: 143468-13-7
• Molecular Formula: C7H5BrN2
• Molecular Weight: 197.034
• Hs Code.: 29339900
• European Community (EC) Number: 821-263-5
• DSSTox Substance ID: DTXSID10457223
• Nikkaji Number: J479.358G
• Wikidata: Q72451432
• Mol file: 143468-13-7.mol

Synonyms:6-bromo-1H-pyrrolo[2,3-b]pyridine;6-Bromo-7-azaindole;143468-13-7;1H-Pyrrolo[2,3-b]pyridine, 6-bromo-;MFCD06659667;SCHEMBL414134;DTXSID10457223;LKXJGVGBEDEAAW-UHFFFAOYSA-N;BCP27062;CS-D0071;BBL103253;STL557063;AKOS006230742;PB21932;6-bromanyl-1H-pyrrolo[2,3-b]pyridine;AS-18912;SY007156;A3099;AM20050814;FT-0650536;EN300-84397;A808072;A884924;J-518307;W-201243

Chemical Property of 6-bromo-1H-pyrrolo[2,3-b]pyridine

Chemical Property:

• Melting Point: 192-195℃
• Refractive Index: 1.728
• Boiling Point: 438.7±37.0 °C(Predicted)
• PKA: 6.76±0.40(Predicted)
• PSA: 28.68000
• Density: 1.771 g/cm³
• LogP: 2.32540
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 195.96361
• Heavy Atom Count: 10
• Complexity: 129

Purity/Quality:

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

6-Bromo-1H-pyrrolo[2,3-b]pyridine ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=NC2=C1C=CN2)Br

Technology Process of 6-bromo-1H-pyrrolo[2,3-b]pyridine

There total 5 articles about 6-bromo-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: 99.0%

1-Benzoyl-6-bromo-1H-pyrrolo<2,3-b>pyridine (143468-12-6) → 6-Bromo-1H-pyrrolo<2,3-b>pyridine (143468-13-7)

Guidance literature:

With sodium hydroxide; In methanol; for 24h; Ambient temperature;

DOI:10.1055/s-1992-26193

Reference yield:

1H-Pyrrolo[2,3-b]pyridine-7-oxide (55052-24-9) → 6-Bromo-1H-pyrrolo<2,3-b>pyridine (143468-13-7)

Guidance literature:

Multi-step reaction with 2 steps

1: 57 percent / hexamethyldisilazene (HMDS) / benzene / 1 h / Ambient temperature

2: 99 percent / aq. NaOH / methanol / 24 h / Ambient temperature

With sodium hydroxide; 1,1,1,3,3,3-hexamethyl-disilazane; In methanol; benzene;

DOI:10.1055/s-1992-26193

Reference yield:

7-Azaindole (271-63-6) → 6-Bromo-1H-pyrrolo<2,3-b>pyridine (143468-13-7)

Guidance literature:

Multi-step reaction with 3 steps

1.1: 3-chloro-benzenecarboperoxoic acid / n-heptane; 1,2-dimethoxyethane / 20 °C / Cooling

1.2: pH 9

2.1: 1,1,1,3,3,3-hexamethyl-disilazane / toluene / 1 h / 20 °C

3.1: sodium hydroxide; methanol / 20 °C

With methanol; 3-chloro-benzenecarboperoxoic acid; 1,1,1,3,3,3-hexamethyl-disilazane; sodium hydroxide; In 1,2-dimethoxyethane; n-heptane; toluene;

upstream raw materials:

1-Benzoyl-6-bromo-1H-pyrrolo<2,3-b>pyridine

1H-Pyrrolo[2,3-b]pyridine-7-oxide

7-Azaindole

Downstream raw materials:

6-amino-1H-pyrrolo<2,3-b>pyridine

6-bromo-1H-pyrrolo[2,3-b]pyridine-3-carboxaldehyde

7-aza-6-phenylaminoindole

N-(3,4-difluorophenyl)-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridin-6-amine

Refernces

• 1、 Cincinelli, Raffaella,Musso, Loana,Merlini, Lucio,Giannini, Giuseppe,Vesci, Loredana,Milazzo, Ferdinando M.,Carenini, Nives,Perego, Paola,Penco, Sergio,Artali, Roberto,Zunino, Franco,Pisano, Claudio,Dallavalle, Sabrina. "7-Azaindole-1-carboxamides as a new class of PARP-1 inhibitors". . p. 1089 - 1103. Retrieved 2014/02/14.
• 2、 -. "NOVEL COMPOUNDS FOR THE TREATMENT OF DISEASES ASSOCIATED WITH AMYLOID OR AMYLOID-LIKE PROTEINS". Page/Page column 83. . Retrieved 2011/11/01.