g 3 3 mmol in anhydrous thf 5 ml added the mixture was stirred at room temperature overnight and poured into water the mixture was extracted twice with ethyl acetate 50 ml and the organic extracts were washed twice with water 50 ml and saturated brine 50 ml the solution was dried over anhydrous sodium sulphate and evaporated to dryness recrystallisation from dichloromethane hexane gave the desired product 0 75 g 56 6 as off white crystals mp 190 191 u00b0 c a mixture of 5 bromo 3 chloro 2 methylthio pyridine 7 5 g 0 031 mol trimethylsilylacetylene 5 3 g 0 053 mol copper i iodide 60 mg 0 32 mmol bis triphenylphosphine palladium ii chloride 0 42 g 0 6 mmol and triethylamine 100 ml was sealed in a 300 ml hastelloy steel bomb and heated with stirring at 80 u00b0 c for 17 hours the mixture was cooled filtered and the precipitate washed with ethyl acetate 100 ml the combined organic solutions were evaporated to dryness under reduced pressure the resultant dark oil was dissolved in hexane 100 ml and washed with water and brine and evaporated under reduced pressure purification of the residue by chromatography over silica 0 2 ethyl acetate hexane gave the desired product 5 6 g 71 as a yellow oil 3 chloro 2 methylthio 5.