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9th April 2013 @ 01:40
Mnr: MNR111-120

Starting material - Bromination of MNR89 at the 7 position - MNR118-1

As for Chlorination of MNR89 To Give MNR99-3

NMR reference  WO2011093684  (A2) ― 2011-08-04 - page 19 step 3

 

Hazard Assessment

HIRAC MNR99.pdf

Procedure

To MNR118-1 (0.180 g, 0.78 mmol) at room temperature was added POCl3 (0.73 mL, 7.79 mmol) under argon and the mixture was heated to reflux for 3 hours during which time the reaction turned a dark brown colour.  The the reaction was then allowed to reach room temperature and was slowly added dropwise to ice (20 mL) in a beaker.  The mixture was then slowly neutralised with sodium bicarbonate.  Once the reaction was fully quenched it was filtered and washed with water to give a pale brown soild (0.086g) 

NMR

 

mnr119-2_filter_1H.pdf
mnr119-2_filter_13C.pdf
mnr119-2_filter.zip

Conclusion

NMR showed mainly starting material with less than 5% product.  The reaction has therefore started to go but has not had long enough.  Reaction needs repeated possibly at a higher temperature and for a longer period of time.

 

The new peaks in the 1H NMR at 9.17 and 8.80 are of different shifts to that of AT-5-6 (9.02 and 8.06) therefore suggesting that the Br substitution has occurred at the 7 position.


AT-5-6-DMSO.pdf

Strings

Starting material

InChI=1S/C6H3BrN2OS/c7-3-1-11-5-4(3)8-2-9-6(5)10/h1-2H,(H,8,9,10)

Product

InChI=1S/C6H2BrClN2S/c7-3-1-11-5-4(3)9-2-10-6(5)8/h1-2H

 

 

Attached Files
MNR119-2_table.PNG
MNR119-2_scheme.png
mnr119-2_filter_13C.pdf
mnr119-2_filter_1H.pdf
mnr119-2_filter.zip
AT-5-6-DMSO.pdf