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15th December 2014 @ 06:08

AEW 205-1 (100 mg, 0.36 mmol, 1.00 equiv.) and AEW 212-1 (54 mg, 0.36 mmol, 1.00 equiv.) were added to toluene (1.5 mL) followed by potassium hydroxide (70 mg, 1.26 mmol, 3.5 equiv.) and 18-crown-6 (6 mg, 0.025 mmol, 0.07 equiv.). The reaction mixture was stirred at 40°C (bath temperature) for 50 min. Heating had failed but TLC recorded and SM found to have been consumed at RT.

The reaction was stopped and cooled before diluting with water (2 mL). The aqueous layer was extracted with EtOAc (4 x 40 mL). The combined organic layers were washed with water (2 x 20 mL), brine (20 mL), dried (MgSO4) and evaporated to yield an orange brown gum.

Purified by flash column chromatography over silica using Biotage Isolera (10 g, pre-packed column, crude loaded in DCM).

Gave two major factions: NMR of second fraction showed desired product x mg.

Data:

AEW 214-1 9:1 DCM:MeOH.jpg

AEW 214-1 crude 300 MHz.pdf

Purified product: 

AEW 214 proton 300.pdf

Fluorine and Proton check

AEW 214 proton 300.pdf
AEW 214-1 fluroine.pdf

Hazard and Risk Assessment:

 

Strings:

InChI=1S/C12H8ClFN4O/c13-10-5-15-6-11-16-17-12(18(10)11)8-1-3-9(4-2-8)19-7-14/h1-6H,7H2

and 

InChI=1S/C9H13NO/c1-10-9(7-11)8-5-3-2-4-6-8/h2-6,9-11H,7H2,1H3

to

InChI=1S/C21H20FN5O2/c1-23-18(15-5-3-2-4-6-15)13-28-20-12-24-11-19-25-26-21(27(19)20)16-7-9-17(10-8-16)29-14-22/h2-12,18,23H,13-14H2,1H3

 

ClC1=CN=CC2=NN=C(C3=CC=C(OCF)C=C3)N21

and

OC[C@H](NC)C1=CC=CC=C1

to

FCOC(C=C1)=CC=C1C2=NN=C3N2C(OC[C@H](NC)C4=CC=CC=C4)=CN=C3

Attached Files
AEW 214-1.png
AEW 214-1.cdxml
AEW 214-1 9:1 DCM:MeOH.jpg
AEW 214-1 crude.zip
AEW 214-1 crude 300 MHz.pdf
AEW 214 proton 300.pdf
AEW 214-1 fluroine.pdf
AEW 214 proton 300.pdf