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15th December 2016 @ 00:00

Outcome

The product was successfully synthesised in XX

Rationale

Attempt to couple the alcohol to the OCHF2 core.

Procedure

AEW 322-1 (203 mg, 1.01 mmol, 1 equiv.) was added to toluene (4 mL) along with AEW 205 (300 mg, 1.01 mmol, 1 equiv.), potassium hydroxide (187 mg, 3.34 mmol, 3.3 equiv.) and 18-crown-6 (21 mg, 0.04 mmol, 0.08 equiv.). The reaction was stirred at rt.

The reaction was diluted with water (20 mL), then extracted with ethyl acetate (3 x 15 mL). The organic layers were washed with water (2 x 20 mL) until the aqueous layer became neutral, followed by brine (15 mL), dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product as a dark brown solid (130.2 mg, 63%). The crude product was purified by flash chromatography on silica (25-100% ethyl acetate in hexanes) to give AEW 323-1 as brown powder ()


Strings


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

and

OCC(N(C)C)C1=CC=C(F)C(F)=C1

to

FC(F)OC(C=C1)=CC=C1C2=NN=C3N2C(OCC(N(C)C)C4=CC=C(F)C(F)=C4)=CN=C3

 

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

and

InChI=1S/C10H13F2NO/c1-13(2)10(6-14)7-3-4-8(11)9(12)5-7/h3-5,10,14H,6H2,1-2H3

to

InChI=1S/C22H19F4N5O2/c1-30(2)18(14-5-8-16(23)17(24)9-14)12-32-20-11-27-10-19-28-29-21(31(19)20)13-3-6-15(7-4-13)33-22(25)26/h3-11,18,22H,12H2,1-2H3


Notes

Theoretical yield = 467 mg

Start at 

Stopped at

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Attached Files
AEW 323-1.rxn
AEW 323-1.cdxml
AEW 323-1.png