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0 °C

A stirred solution of N-[3-bromo-4-(pyrid-4-ylmethylthio)phenyl]-2'-methyl-4'-(5-methyl-1,2,4-oxadiazol-3-yl)biphenyl-4-carboxamide (D 16) (1.41 g, 2.46 mmol) in dry DMF (15 ml) was treated with methyl iodide (0.184 ml, 2.95 mmol). After 60 h, the reaction mixture was evaporated under reduced pressure and the residue was triturated with ethyl acetate. The resultant brown solid was filtered off and dried in vacuo. It was redissolved in a mixture of ethanol (150 ml) and water (75 ml), cooled to 0° C. and treated with sodium borohydride (0.165 g, 4.35 mmol) slowly with stirring. After 1 h, the reaction mixture was treated with potassium carbonate solution (50 ml). The resultant suspension was extracted with dichloromethane (3×100 ml) and the combined organic layers were dried (Na2SO4) and evaporated under reduced pressure to give a brown solid, which was purified by silica gel chromatography (10% MeOH/CH2Cl2 as eluant) to give the title compound as a yellow oil (0.680 g, 47%).

1. customthe reaction mixture was evaporated under reduced pressure
2. customthe residue was triturated with ethyl acetate
3. filtrationThe resultant brown solid was filtered off
4. customdried in vacuo
5. dissolutionIt was redissolved in a mixture of ethanol (150 ml) and water (75 ml)
6. waitAfter 1 h
7. extractionThe resultant suspension was extracted with dichloromethane (3×100 ml)
8. dry with materialthe combined organic layers were dried (Na2SO4)
9. customevaporated under reduced pressure
10. customto give a brown solid, which
11. customwas purified by silica gel chromatography (10% MeOH/CH2Cl2 as eluant)