All Blogs | Help | Support | About
x This LabTrove instance has just been upgraded to 2.3, to see what new check out the documentation, http://www.labtrove.org/documentation/
11th November 2013 @ 00:38

To a well stirred solution of AEW 95-1 (1 g,  3.8 mmol) in CH2Cl2 (60 mL) was added PhI(OAc)2 (1.22 g,  3.8 mmol) and the resulting reaction mixture was stirred at room temperature for 1 h. Aliquot showed SM still present so monitored for a further 1.5 h and then a saturated aqueous solution of sodium hydrogen carbonate was added and the reaction mixture was extracted into CH2Cl2 (3 x 120 mL). The aqueous layer contains insoluble precipitate. Insoluble in CH2Cl2, EtOAc, MeOH. Want to try Joie Garfunkle's suggestion of 2-MeTHF but awaiting this solvent. Combined organic layers were dried over MgSO4, filtered and evaporated to give an orange crystalline solid (1.25 g). Crude NMR shows product, iodobenzene, PIDA and AcOH.

Column 2:1 hex/EtOAc then 100% EtOAc to give two fractions:

AEW 97-7 A pure product (165 mg, 0.65 mmol, 17% yield)

 

and

 

AEW 97-7 B impure fraction (50 mg)

Crude 1H NMR (CDCl3):

AEW 97-7 crude.pdf

Iodobenzene

AEW 97-7 crude.pdf

PIDA

PIDA.pdf
Hazard and Risk Assessment:

See 4-(5-chloro-[1,2,4]triazolo[4,3-a]pyrazin-3-yl)benzonitrile (AEW 97-1) 

InChi:

InChI=1S/C12H8ClN5/c13-11-7-15-8-12(17-11)18-16-6-10-3-1-9(5-14)2-4-10/h1-4,6-8H,(H,17,18)/b16-6+

to

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

 

Linked Posts
Attached Files
AEW 97-7 crude.pdf
AEW 97-7 crude.mnova
Iodobenzene.pdf
AEW 97-7 crude.zip
PIDA.pdf