All Notebooks | Help | Support | About
27th July 2016 @ 23:36

GitHub Issue #400 Resynthesised as part of "Frontrunner" campaign.

(xx mg, 0.xx mmol, xx% yield)

Starting material synthesis: 

Procedure:

JU 8 (310 mg, 1.17 mmol, 1 equiv.), potassium hydroxide (229 mg, 4.09 mmol, 3.5 equiv.) and 18-crown-6 (21.6 mg, 81.8 μmol, 0.07 equiv.) were stirred in toluene (11 mL) and 2-(3,4-difluorophenyl)ethanol (185 mg, 1.17 mmol, 1 equiv.) was added and the reaction mixture stirred at rt for 30 mins. TLC showed reaction complete (9:1 EtOAc/hex)


Water (20 mL) was added and the mixture was extracted with EtOAc (3 x 40 mL). Combined organic layers were washed with water (20 mL), brine (20 mL), dried (MgSO4) filtered and evaporated to give a pale yellow solid which was purified by flash column chromatography using the Biotage IsoleraTM with handpacked 50 g column and EtOAc gradient. One fraction collected and evaporated to yield the desired product as a pearlescent cream solid (218 mg, 0.051 mmol, 44% yield).

 

Data:

 

AEW 302-1 200 MHZ.png
AEW 302-1 200 MHZ.mnova
AEW 302-1 200 MHZ.jcamp
AEW 302-1 200 MHz.zip

Hazard and Risk Assessment:

HIRAC AEW 296-1 .doc

Strings:

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

to

FC1=C(F)C=CC(CCOC2=CN=CC3=NN=C(C4=CC=C(Cl)C=C4)N32)=C1

InChI=1S/C11H5ClF3N5/c12-8-4-16-5-9-18-19-10(20(8)9)6-1-2-7(17-3-6)11(13,14)15/h1-5H

to

InChI=1S/C19H13ClF2N4O/c20-14-4-2-13(3-5-14)19-25-24-17-10-23-11-18(26(17)19)27-8-7-12-1-6-15(21)16(22)9-12/h1-6,9-11H,7-8H2


Attached Files
AEW 302-1.cdxml
AEW 302-1.png
AEW 302-1 200 MHZ.png
AEW 302-1 200 MHZ.mnova
AEW 302-1 200 MHZ.jcamp
AEW 302-1 200 MHz.zip