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7th December 2016 @ 08:55

Outcome

Ref: EGT 165-1


 

Rationale

Attempt to displace the bromine with dimethylamine.

Procedure

EGT 164-1 (580 mg, 2.08 mmol, 1 equiv.) was dissolved in DMF (6 mL). Dimethylamine solution (33% in alcohol, 0.38 mL, 2.08 mmol, 1 equiv.) and K2CO3 (862 mg, 6.23 mmol, 3 equiv.) were added and the reaction stirred at rt. The reaction was filtered and the solvent removed. The residue was partitioned between EtOAc and water. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine, dried (Na2SO4), filtered and concentrated under reduced pressure to give the crude product as a yellow oil (800 mg - further drying required, 590 mg).

NMR

AEW 321-1 crude proton.mnova
AEW 321-1 crude proton.jcamp
AEW 321-1 crude proton.png
AEW 321-1.zip

Checked NMR = good but DMF

AEW 321-1.zip

Dissolved in EtOAc and washed with water (x3) then brine, the dried dried (Na2SO4), filtered and concentrated under reduced pressure to give ..

 

Strings

O=C(OCC)C(Br)C1=CC(F)=C(F)C=C1

to

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

 

InChI=1S/C10H9BrF2O2/c1-2-15-10(14)9(11)6-3-4-7(12)8(13)5-6/h3-5,9H,2H2,1H3

to

InChI=1S/C12H15F2NO2/c1-4-17-12(16)11(15(2)3)8-5-6-9(13)10(14)7-8/h5-7,11H,4H2,1-3H3


Notes

Theoretical yield = 506 mg

Start reaction at 4pm Mon

Stopped at 11 am Tue

 

Ref: WO 1999008697 A1

Attached Files
AEW 322-1.rxn
AEW 322-1.cdxml
AEW 322-1.png
AEW 321-1.zip
AEW 321-1 crude proton.png
AEW 321-1 crude proton.jcamp
AEW 321-1 crude proton.mnova