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29th June 2015 @ 09:37

Reaction Scheme

Procedure

AEW 204 (~29.1 mmol) was stirred into CH2Cl2 (250 mL). PhI(OAc)(9.37 g, 29.1 mmol) was added and the resulting solution was stirred at room temperature overnight. The orange/brown suspension turned to a read/orange solution. The reaction was quenched by addition of a saturate aqueous solution of sodium hydrogen carbonate (150 mL) and diluted with dichloromethane (50 mL). Organic layers were separated and aqueous layers washed with dichloromethane (100 ml). Combined organic layers were washed with a saturate aqueous solution of sodium hydrogen carbonate (100 mL), brine (100 mL), dried (MgSO4), filtered and evaporated to give a brown/orange sludge. Ethyl Acetate (~90 mL) was added and the mixture heated to ~70 ˚C with intermittent sonication, until all of the solid had dissolved. The solution was left to cool to room temperature and a solid precipated from the solution. The mixture was cooled in ice water bath for a further 30 minutes and then filtered and washed with cod ethyl acetate (20 mL) to yield a gold solid that was dried at the high vac (4.49 g, 15.1 mmol, 52% yield). (NMR showed pure product). The residue was reduced to ~50 mL and left in the fridge overnight. A red/orange solid had formed at the bottom of the flask and was broken up by sonication. The solid was filtered and washed with cold ethyl acetate (~15 mL) to give a red/orange crystalline material that was dried at the high vac (1.71 g, 5.76 mmol, 20% yield). 

TLC shows product in mother liquor, to be columned. Current total: (6.2 g, 72% yield)

 

Data:

AEW 205 second cryst 300 MHz.pdf
AEW 205 2nd recryst.zip
205 crude first batch.zip

HIRAC

 See 5-chloro-3-(4-(difluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyrazine (JU 19-1)

InChI strings

InChI=1S/C12H9ClF2N4O/c13-10-6-16-7-11(18-10)19-17-5-8-1-3-9(4-2-8)20-12(14)15/h1-7,12H,(H,18,19)/b17-5+

to

InChI=1S/C12H7ClF2N4O/c13-9-5-16-6-10-17-18-11(19(9)10)7-1-3-8(4-2-7)20-12(14)15/h1-6,12H

SMILES

ClC1=CN=CC(N/N=C/C2=CC=C(OC(F)F)C=C2)=N1

to

ClC1=CN=CC2=NN=C(C3=CC=C(OC(F)F)C=C3)N21

Linked Entries
Attached Files
AEW 205 2nd recryst.zip
AEW 205 second cryst 300 MHz.pdf
205 crude first batch.zip