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21st September 2016 @ 03:36

NB used crude AEW 232-3 prior to NMR owing to time constraints - will check validity of SM asap.

 

 

AEW 232-3 (based on 1.96 mmol) was dissolved in EtOH (8 mL). CuCl2.2H2O (17 mg, 0.08 mmol, 5 mol%) was added and the reaction heated at reflux for 40 mins. TLC no SM

The solvent was removed and the crude black oil was columned using the Biotage Isolera - EtOAc then 10-20% MeOH in DCM. Multiple black fractions collected.

 

Data:

TLC

AEW 317-1 (EtOAc).JPG

AEW 317-1 Frac 2 NMR 300 MHz

problem accessing NMR data but looks promising

Strings:

FC(OC(C=C1)=CC=C1C2=NN=C3N2C(OCC(COC4OCCCC4)C5=CC=CC=C5)=CN=C3)F

to

OCC(C1=CC=CC=C1)COC2=CN=CC3=NN=C(C4=CC=C(OC(F)F)C=C4)N32

InChI=1S/C21H18F2N4O3/c22-21(23)30-17-8-6-15(7-9-17)20-26-25-18-10-24-11-19(27(18)20)29-13-16(12-28)14-4-2-1-3-5-14/h1-11,16,21,28H,12-13H2

to

InChI=1S/C21H18F2N4O3/c22-21(23)30-17-8-6-15(7-9-17)20-26-25-18-10-24-11-19(27(18)20)29-13-16(12-28)14-4-2-1-3-5-14/h1-11,16,21,28H,12-13H2

Attached Files
AEW 317-1.rxn
AEW 317-1.cdx
AEW 317-1.png
AEW 317-1 (EtOAc).JPG
AEW 317-1 (EtOAc).JPG