1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester

Base Information

• Chemical Name: 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester
• CAS No.: 1018950-15-6
• Molecular Formula: C12H14N2O2
• Molecular Weight: 218.25
• Mol file: 1018950-15-6.mol

Synonyms:1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester;tert-butyl 1H-pyrrolo[3,2-b]pyridine-1-carboxylate

Chemical Property of 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester

Chemical Property:

• Melting Point: 69-71 °C
• Boiling Point: 327.2±34.0 °C(Predicted)
• PKA: 5.34±0.30(Predicted)
• PSA: 44.12000
• Density: 1.14±0.1 g/cm3(Predicted)
• LogP: 2.81950
• Storage Temp.: Sealed in dry,Room Temperature

Purity/Quality:

98%min ^*data from raw suppliers

tert-Butyl1H-pyrrolo[3,2-b]pyridine-1-carboxylate 97% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester

There total 4 articles about 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 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: 100.0%

1H-pyrrolo[3,2-b]pyridine (272-49-1) + di-tert-butyl dicarbonate (24424-99-5) → 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester (1018950-15-6)

Guidance literature:

With dmap; In acetonitrile; at 20 ℃; for 3h; Inert atmosphere;

DOI:10.1002/cbic.200900651

Reference yield: 78.0%

tert-butyl 3-iodo-1H-pyrrolo[3,2-b]pyridine-1-carboxylate (1316228-21-3) + C9H16NO4Zn(1+)*I(1-) → 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester (1018950-15-6) + C21H29N3O6

Guidance literature:

With tris(dibenzylideneacetone)dipalladium⁽⁰⁾ chloroform complex; DavePhos; at 35 ℃; Reagent/catalyst; Inert atmosphere;

DOI:10.1016/j.bmc.2018.03.037

Reference yield: 53.0%

tert-butyl carbazate (4248-19-5) + (E)-3-bromo-2-(2-bromovinyl)pyridine (1196079-77-2) → 1H-pyrrolo[3,2-b]pyridine-1-carboxylic acid 1,1-dimethylethyl ester (1018950-15-6)

Guidance literature:

With palladium diacetate; caesium carbonate; bis[2-(diphenylphosphino)phenyl] ether; In 1,4-dioxane; at 100 ℃; Inert atmosphere;

DOI:10.1016/j.tet.2009.08.046

upstream raw materials:

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

di-tert-butyl dicarbonate

tert-butyl carbazate

(E)-3-bromo-2-(2-bromovinyl)pyridine

Downstream raw materials:

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

2,3-dihydro-1H-pyrrolo[3,2-b]pyridine

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

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

Refernces

• 1、 Yamawaki, Kenji,Nomura, Takashi,Yasukata, Tatsuro,Tanimoto, Norihiko,Uotani, Koichi,Miwa, Hideaki,Yamano, Yoshinori,Takeda, Kei,Nishitani, Yasuhiro. "A novel series of parenteral cephalosporins exhibiting potent activities against both Pseudomonas aeruginosa and other Gram-negative pathogens. Part 2: Synthesis and structure-activity relationships". . p. 1632 - 1647. Retrieved 2008.
• 2、 -. "NOVEL SUBSTITUTED TETRAHYDROQUINOLIN COMPOUNDS AS INDOLEAMINE 2,3-DIOXYGENASE (IDO) INHIBITORS". Page/Page column 167. . Retrieved 2019/05/22.
• 3、 -. "BICYCLIC DIAMINES AS JANUS KINASE INHIBITORS". Paragraph 0096. . Retrieved 2019/01/04.