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30th January 2018 @ 18:34

Masses and measurements:

SnAr product - 0.05g, 0.116mmol

NaOtBu - 0.0156g, 0.162mmol

Morpholine - 0.02mL, 0.139mmol

Pd2(dba)2 - 0.53mg, 0.583μmol

John Phos- 1.158mg, 5.22μmol

Toluene - 2mL


Procedure:


(SnAr product) 3-(4-bromophenethoxy)-[1,2,4]triazolo[4,3,a]pyrazine (0.05g, 0.116mmol) was dissolved in toluene (2mL) in a RBF and the base, NaOtBu, (0.0516g, 0.162mmol) was added. The ligand, John Phos (1.158mg, 5.22μmol) and the amine, morpholine (0.02mL, 0.139mmol) were added to the reaction mixture. Lastly, the palladium source, Pd2(dba)(0.53mg, 0.58μmol) was added to the RBF and the mixture was left to stir and heat to 80°C until TLC analysis showed any sign of reaction. 

TLC step 5 3 cropped 1.jpg
               
TLC step 5 3 cropped 2.jpg
                       
TLC step 5 3 cropped 3.jpg

 TLC after 1 day                     TLC after 1 week                          TLC with 100% DCM                   

The reaction mixture was seperated using 2M HCl givng an orange layer and a pale yellow layer. TLC analysis was done using the organic top layer. After 1 day TLC analysis (98% DCM, 2% methanol) still showed presence of the starting material. After 1 week TLC analysis confirmed less starting material and possibly a new product. Next the whole top organic layer wasextracted and rotary evapoaretd leaving a dark green crude product. The crude product was run on a flash column (2% methanol, 98% DCM) and TLC analysis (2% methanol, 98% DCM) confirmed the presence of a possible product in test tube 16-25. These test tubes were collected and rotary evapoarted, however H NMR analysis confirmed no presence of the desired final product. 

                             

TLC step 5 2.jpg
                       

                    TLC analysis Test tubes 21-35                

 

 
Attached Files
TLC step 5 3 cropped 1.jpg
TLC step 5 3 cropped 2.jpg
TLC step 5 3 cropped 3.jpg
TLC step 5 2.jpg