4',3'-d]pyrrole

Base Information

• Chemical Name: 4',3'-d]pyrrole
• CAS No.: 1266527-30-3
• Molecular Formula: C10H5ClFN3
• Molecular Weight: 221.62
• Mol file: 1266527-30-3.mol

Synonyms:4',3'-d]pyrrole;6-Chloro-5-fluoro-9H-dipyrido[2,3-b;6-chloro-5-fluoro-9H-pyrrolo[2,3-b:5,4-c']dipyridine

Chemical Property of 4',3'-d]pyrrole

Chemical Property:

• Boiling Point: 433.8±40.0 °C(Predicted)
• PKA: 10?+-.0.50(Predicted)
• Density: 1.599±0.06 g/cm3(Predicted)

Purity/Quality:

95% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 4',3'-d]pyrrole

There total 8 articles about 4',3'-d]pyrrole 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: 81.0%

6'-chloro-2,5'-difluoro-[3,4']bipyridinyl-3'-ylamine (1312755-63-7) → 6-chloro-5-fluoro-9H-pyrrolo[2,3-b:5,4-c']dipyridine (1266527-30-3)

Guidance literature:

With lithium hexamethyldisilazane; In tetrahydrofuran; at 5 - 30 ℃; for 6h; Large scale;

DOI:10.1021/acs.oprd.5b00105

Reference yield: 30.0%

3-chloro-N-(6-chloro-5-fluoropyridin-3-yl)pyridin-2-amine → 6-chloro-5-fluoro-9H-pyrrolo[2,3-b:5,4-c']dipyridine (1266527-30-3)

Guidance literature:

3-chloro-N-(6-chloro-5-fluoropyridin-3-yl)pyridin-2-amine; With n-butyllithium; In tetrahydrofuran; hexane; at -70 - -50 ℃;

With zinc(II) chloride; In tetrahydrofuran; hexane; at -65 - 20 ℃; Inert atmosphere;

With bis(tri-t-butylphosphine)palladium⁽⁰⁾; In tetrahydrofuran; hexane; at 75 ℃; for 18h; Inert atmosphere;

DOI:10.1021/acs.oprd.5b00105

Reference yield:

5-bromo-2-chloro-3-fluoro-pyridine (831203-13-5) → 6-chloro-5-fluoro-9H-pyrrolo[2,3-b:5,4-c']dipyridine (1266527-30-3)

Guidance literature:

Multi-step reaction with 5 steps

1.1: caesium carbonate / 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾ / 1,4-dioxane / 24 h / 85 °C

2.1: N,N,N,N,-tetramethylethylenediamine; n-butyllithium / hexane; diethyl ether / 1.5 h / -78 - -20 °C / Inert atmosphere

2.2: -78 - 20 °C

3.1: trifluoroacetic acid / dichloromethane / 1.5 h / 20 °C

4.1: potassium fluoride / bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II) / acetonitrile; water / 2 h / 90 °C

5.1: sodium hexamethyldisilazane / tetrahydrofuran / 1 h / 20 - 40 °C

With potassium fluoride; n-butyllithium; N,N,N,N,-tetramethylethylenediamine; sodium hexamethyldisilazane; caesium carbonate; trifluoroacetic acid; tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In tetrahydrofuran; 1,4-dioxane; diethyl ether; hexane; dichloromethane; water; acetonitrile;

upstream raw materials:

5-bromo-2-chloro-3-fluoro-pyridine

(6-chloro-5-fluoropyridin-3-yl)carbamicacid tert-butyl ester

(6-chloro-5-fluoro-4-iodopyridin-3-yl)carbamic acid tert-butyl ester

6-chloro-5-fluoro-4-iodo-pyridin-3-amine

Refernces

• 1、 -. "1, 7 - DIAZACARBAZOLES AND THEIR USE IN THE TREATMENT OF CANCER". . . Retrieved 2011/07/07.