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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: [data]14363[/data] [data]14367[/data] Purified product: [data]14397[/data] Fluorine and Proton check [data]14985[/data][data]14983[/data] 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