The reaction of an aromatic heterocycle with a proton is called a protonation. One of articles about this theory is 《A New Flow Methodology for the Expedient Synthesis of Drug-Like 3-Aminoindolizines》. Authors are Lange, Paul P.; Bogdan, Andrew R.; James, Keith.The article about the compound:Methyl 6-bromonicotinatecas:26218-78-0,SMILESS:C1=NC(=CC=C1C(=O)OC)Br).Category: tetrahydrofurans. Through the article, more information about this compound (cas:26218-78-0) is conveyed.
A flow-based synthesis of diversely functionalized indolizines and their aza-analogs is described. These drug-like heterocycles were generated via a tandem Sonogashira/cycloisomerization sequence, starting from widely available 2-bromopyridines and alkynes, employing a simple catalyst system together with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) as base. E.g., in presence of PdCl2(PPh3)2, CuI, and NEt3, followed by addition of DBU in DMF, Sonogashira/cycloisomerization of Me 6-bromonicotinate and N-methyl-N-propargylbenzylamine gave 71% indolizine derivative (I). The use of flow technol. allows a straightforward and rapid access to a variety of novel compounds, and enables linear scale-up from milligram- to gram-scales without a decrease in yield.
The article 《A New Flow Methodology for the Expedient Synthesis of Drug-Like 3-Aminoindolizines》 also mentions many details about this compound(26218-78-0)Category: tetrahydrofurans, you can pay attention to it, because details determine success or failure
Reference:
Tetrahydrofuran – Wikipedia,
Tetrahydrofuran | (CH2)3CH2O – PubChem