tert-butyl 5H-pyrido[3,2-b]indole-2-carboxylate

Base Information

• Chemical Name: tert-butyl 5H-pyrido[3,2-b]indole-2-carboxylate
• CAS No.: 1300728-36-2
• Molecular Formula: C₁₆H₁₆N₂O₂
• Molecular Weight: 268.315
• Mol file: 1300728-36-2.mol

Synonyms:

Chemical Property of tert-butyl 5H-pyrido[3,2-b]indole-2-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl 5H-pyrido[3,2-b]indole-2-carboxylate

There total 2 articles about tert-butyl 5H-pyrido[3,2-b]indole-2-carboxylate 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: 55.6%

tert-butyl 5-[(2-chlorophenyl)amino]picolinate (1300728-31-7) → tert-butyl 5H-pyrido[3,2-b]indole-2-carboxylate (1300728-36-2) + 3-tert-butoxycarbonyl-β-carboline (93835-05-3)

Guidance literature:

With palladium diacetate; potassium carbonate; tri tert-butylphosphoniumtetrafluoroborate; In N,N-dimethyl acetamide; at 120 ℃; for 16h; regioselective reaction; Inert atmosphere; Sealed vessel;

DOI:10.1021/jo200425m

Reference yield:

tert-butyl 5-bromopyridine-2-carboxylate (845306-08-3) + o-chloroaniline (95-51-2) → tert-butyl 5H-pyrido[3,2-b]indole-2-carboxylate (1300728-36-2) + 3-tert-butoxycarbonyl-β-carboline (93835-05-3)

Guidance literature:

Multi-step reaction with 2 steps

1: palladium diacetate; XPhos; caesium carbonate / toluene / 110 °C / Inert atmosphere; Sealed tube

2: palladium diacetate; tri tert-butylphosphoniumtetrafluoroborate; potassium carbonate / N,N-dimethyl acetamide / 16 h / 120 °C / Inert atmosphere; Sealed tube

With palladium diacetate; potassium carbonate; caesium carbonate; tri tert-butylphosphoniumtetrafluoroborate; XPhos; In N,N-dimethyl acetamide; toluene; 1: |Buchwald-Hartwig Coupling / 2: |Heck Reaction;

DOI:10.1039/c5ob01572c

upstream raw materials:

tert-butyl 5-[(2-chlorophenyl)amino]picolinate

tert-butyl 5-bromopyridine-2-carboxylate

o-chloroaniline

Refernces

• 1、 Namjoshi, Ojas A.,Gryboski, Angelica,Fonseca, German O.,Van Linn, Michael L.,Wang, Zhi-Jian,Deschamps, Jeffrey R.,Cook, James M.. "Development of a two-step route to 3-PBC and βcCt, two agents active against alcohol self-administration in rodent and primate models". experimental part. p. 4721 - 4727. Retrieved 2011/07/08.