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30th August 2016 @ 03:11

AEW (200 mg, 0.78 mmol, 1.0 equiv.), potassium hydroxide (154 mg, 2.74 mmol, 3.5 equiv.) and 18-crown-6 (15 mg, 0.05 mmol, 0.07 equiv.) were stirred in toluene (6 mL) and AEW alcohol (147 mg, 0.78 mmol, 1.0 equiv.) was added and the reaction mixture stirred at 40 ˚ C for 30 mins. 

TLC showed reaction complete (5:2 EtOAc/hex)

Directly applied crude mixture to Biotage Isolera and obtained one fraction as a cream solid (208 mg, 0.51 mmol, 65% yield).

AEW 313-1.JPG

Data:

300 MHz NMR Recryst:

AEW 313-1.png
AEW 313-1.jcamp
AEW 313-1.mnova
AEW 313-1.zip

Strings

InChI=1S/C12H6ClN5/c13-10-6-15-7-11-16-17-12(18(10)11)9-3-1-8(5-14)2-4-9/h1-4,6-7H

and

InChI=1S/C9H10F2O2/c1-13-9(5-12)6-2-3-7(10)8(11)4-6/h2-4,9,12H,5H2,1H3

to

InChI=1S/C21H15F2N5O2/c1-29-18(15-6-7-16(22)17(23)8-15)12-30-20-11-25-10-19-26-27-21(28(19)20)14-4-2-13(9-24)3-5-14/h2-8,10-11,18H,12H2,1H3

 

ClC1=CN=CC2=NN=C(C3=CC=C(C#N)C=C3)N21

and

OCC(OC)C1=CC(F)=C(F)C=C1

to

FC1=C(F)C=CC(C(OC)COC2=CN=CC3=NN=C(C4=CC=C(C#N)C=C4)N32)=C1

Attached Files
AEW 313-1.png
AEW 313-1.cdxml
AEW 313-1.JPG
AEW 314-1 300 MHz Proton.png
AEW 314-1 300 MHz Proton.mnova
AEW 313-1.jcamp
AEW 313-1.mnova
AEW 313-1.zip