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4th December 2017 @ 15:40

NH1-008

Synthesis of final product using Buchwald-Hartwig cross-coupling - on a larger scale

Mechanism

 

 
mechanism final step.jpg
Compound Data(mr/density) 

 Amount

 mMol Eqv 
NH1-007 412.9  0.100g  0.24 
Toluene 4.00ml  -
Pyrrollidine  71.2/0.85g/ml  0.048ml 0.28 1.2 
NaOtBu 96.1  0.0323g  0.34  1.4 
Pd(dBA)2  575.00 0.00069g  0.0012  0.50% 
Johns Phos 298.40 0.00322g 0.0108 4.5%

Procedure- NH1-008

NH1-007 (0.100g, 0.24mmol) was dissolved in degassed toluene (4.00mL). Pyrrolidine (0.048mL,0.28mmol) was added dropwise. John Phos (0.00322g, 0.0108mmol) was added followed by the base, NaOtBu (0.0323g, 0.34mmol). Pd(dBA)2 (0.00069g, 0.0012mmol) was added and the reaction was left to stir at 80 degrees for 7 days.

NH1-008 was separated using HCl and EtOAc. This was then dried using MgSO4, filtered and dried in vacuo. TLC was carried out (5% MeOH/95% DCM) and is shown below.

final TLC.jpg

1H NMR of NH1-008 was taken in chloroform. The NMR did not show the significant product peaks. To confirm this, NH1-008 was purified via flash column chromatography (2% MeOH/98% DCM). The TLC concluded a potential product in vials from 9-16. These were collected and dried in vacuo. 1HNMR was taken but unfortunately the analysis concluded that this reaction did not work as the spectra was same as the starting material.

Attached Files
final TLC.jpg