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4th December 2014 @ 15:36

Reaction Scheme 

Experimental Procedure

JS 11-1 [Synthesis of 4-(5-chloro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)benzonitrile (JS 11-1)]  (80 mg, 0.315 mmol) was dissolved in toluene (2 mL) and then treated with 2-(2-chlorophenyl)ethanol (0.05 mL, 0.377 mmol). KOH (58 mg, 1 mmol) & 18-crown-6 (9 mg, 0.032 mmol) were then added and the mixture was allowed to stir for 1 hour. 

The mixture was cooled to room temperature before water (6 mL) was added. The phases were separated and the aqueous layer was washed with EtOAc (4 x 5 mL). The organic layer was then washed with water until the aqueous later became neutral. The combined organic layers were dried over Na2SO4 and filtered before removing solvents in vacuo to produce the crude product. An attempt at purifing the product was carried out using dry flash column chromatography however this was unsuccesful.

SMILES 

ClC(C=CC=C1)=C1CCOC2=CC=CC3=NN=C(C4=CC=C(C#N)C=C4)N32

to

ClC(C=CC=C1)=C1CCOC2=CC=CC3=NN=C(C4=CC=C(C#N)C=C4)N32

InChI Strings 

InChI=1S/C21H15ClN4O/c22-18-5-2-1-4-16(18)12-13-27-20-7-3-6-19-24-25-21(26(19)20)17-10-8-15(14-23)9-11-17/h1-11H,12-13H2

to

InChI=1S/C21H15ClN4O/c22-18-5-2-1-4-16(18)12-13-27-20-7-3-6-19-24-25-21(26(19)20)17-10-8-15(14-23)9-11-17/h1-11H,12-13H2

Attached Files
JS 13-1.png