N-Boc-b-nornicotryine

Base Information

• Chemical Name: N-Boc-b-nornicotryine
• CAS No.: 215187-35-2
• Molecular Formula: C₁₄H₁₆N₂O₂
• Molecular Weight: 244.293
• DSSTox Substance ID: DTXSID70399074
• Nikkaji Number: J991.618K
• Wikidata: Q82201416
• Mol file: 215187-35-2.mol

Synonyms:N-Boc-b-nornicotryine;215187-35-2;Tert-butyl 2-pyridin-3-ylpyrrole-1-carboxylate;DTXSID70399074;FT-0663545;tert-butyl 2-(pyridin-3-yl)-1H-pyrrole-1-carboxylate;1,1-Dimethylethyl 2-(3-pyridinyl)-1H-pyrrole-1-carboxylate;2-(3-Pyridinyl)-1H-pyrrole-1-carboxylic acid tert-butyl ester

Chemical Property of N-Boc-b-nornicotryine

Chemical Property:

• Boiling Point: 378.6±34.0 °C(Predicted)
• PKA: 4.81±0.12(Predicted)
• Density: 1.09±0.1 g/cm3(Predicted)
• Storage Temp.: Amber Vial, Refrigerator, Under Inert Atmosphere
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 244.121177757
• Heavy Atom Count: 18
• Complexity: 299

Purity/Quality:

97% ^*data from raw suppliers

N-Boc-b-nornicotryine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1C=CC=C1C2=CN=CC=C2

Technology Process of N-Boc-b-nornicotryine

There total 6 articles about N-Boc-b-nornicotryine 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: 96.0%

3-Chloropyridine (626-60-8) + N-boc-2-pyrroleboronic acid (135884-31-0) → tert-butyl 2-(pyridin-3-yl)-1H-pyrrole-1-carboxylate (215187-35-2)

Guidance literature:

3-Chloropyridine; N-boc-2-pyrroleboronic acid; With palladium diacetate; (R)-6-dicyclohexylphoshino-6'-diphenylphosphino-3,3'-dimethoxy-2,2',4,4'-tetramethyl-1,1'-biphenyl; In dodecane; butan-1-ol; at 25 ℃; for 0.0833333h; Glovebox; Inert atmosphere;

With cesiumhydroxide monohydrate; In dodecane; water; butan-1-ol; at 25 ℃; Inert atmosphere; Glovebox;

DOI:10.1002/ejoc.201200918

Reference yield: 93.0%

3-Bromopyridine (626-55-1,163928-56-1) + 1-N-Boc-pyrrole-2-boronic acid → tert-butyl 2-(pyridin-3-yl)-1H-pyrrole-1-carboxylate (215187-35-2)

Guidance literature:

With tris-(dibenzylideneacetone)dipalladium⁽⁰⁾; potassium fluoride dihydrate; tri-tert-butylphosphonium tetrafluoroborate; In tetrahydrofuran; at 20 ℃; Inert atmosphere;

DOI:10.1002/adsc.201000267

Reference yield: 82.0%

3-Bromopyridine (626-55-1,163928-56-1) + N-boc-2-pyrroleboronic acid (135884-31-0) → tert-butyl 2-(pyridin-3-yl)-1H-pyrrole-1-carboxylate (215187-35-2)

Guidance literature:

With C₄₃H₃₇ClFeNiP₂*C₄H₈O; potassium carbonate; In tetrahydrofuran; acetonitrile; at 50 ℃; for 12h; Inert atmosphere;

DOI:10.1002/anie.201207428

upstream raw materials:

3-Bromopyridine

N-boc-2-pyrroleboronic acid

3-Chloropyridine

pyridin-3-ylamine

Refernces

• 1、 Mishra, Sanket J.,Ghosh, Suman,Stothert, Andrew R.,Dickey, Chad A.,Blagg, Brian S. J.. "Transformation of the non-selective aminocyclohexanol-based Hsp90 inhibitor into a Grp94-seletive scaffold". . p. 244 - 253. Retrieved 2017/12/30.
• 2、 Yang, Junfeng,Liu, Sijia,Zheng, Jian-Feng,Zhou, Jianrong. "Room-temperature Suzuki-Miyaura coupling of heteroaryl chlorides and tosylates". supporting information. p. 6248 - 6259,12. Retrieved 2020/09/16.