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10th March 2013 @ 23:29
Mnr: MNR101-110

Starting material from - Bromination of MNR100-2 to give MNR101-2

and - Synthesis of Boronic Acid Pinacol Ester - MNR103-1

 As for - Arylation of MNR101-2 to give MNR104-1

 

Hazard Assessment

HIRAC MNR103.pdf

Procedure

To a degassed solution of IPA (2 mL) and aqueous potassium carbonate (1 M, 0.33 mL) was added MNR101-2 (0.05 g, 0.17 mmol) and MNR103-1 (0.057g, 0.2 mmol) and the reaction mixture further degassed for 5 minutes. Pd(dppf)Cl2 (0.024 g, 0.03 mmol) was added and the reaction mixture stirred at 80 °C overnight (15 hours).  The reaction was allowed to cool to room temperature and was filtered through celite and rinsed with EtOAc (3 x 15 mL).  

TLC

 

SANY0066.JPG
75% EtOAc/Hex

 

 

Column - 75-100% EtOAc/Hex

Fracs 60-85 o.o18 g, 0.05 mmol, 29% as a pale brown solid.

** It was found that the pure product did not disolve too well in EtOAc so it's fair to say that some product may have been lost on the the column and therefore explaining the low yield.

 

NMR

 

mnr106-1_col_1H.pdf
mnr106-1_col.zip

 

Conclusion

Successful synthesis of the title compound allbeit in low yield possibly due to it's poor solubility in EtOAc. 

Strings 

Starting material

InChI=1S/C10H10BrN3OS/c11-8-5-7-9(16-8)10(13-6-12-7)14-1-3-15-4-2-14/h5-6H,1-4H2

InChI=1S/C12H18BNO4S/c1-11(2)12(3,4)18-13(17-11)9-6-5-7-10(8-9)19(14,15)16/h5-8H,1-4H3,(H2,14,15,16)

 

Product

InChI=1S/C16H16N4O3S2/c17-25(21,22)12-3-1-2-11(8-12)14-9-13-15(24-14)16(19-10-18-13)20-4-6-23-7-5-20/h1-3,8-10H,4-7H2,(H2,17,21,22)

Linked Posts
Attached Files
MNR106_scheme.png
MNR106-1_table.PNG
SANY0066.JPG
mnr106-1_col_1H.pdf
mnr106-1_col.zip