Ethyl trifluoromethanesulphonate → HCID 24798511, compound

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Reaction Steps

2.40 g (6.16 mmol) of 4-(3-acetyl-2-methyl-5-oxo-1,4,5,6-tetrahydro-1,6-naphthyridin-4-yl)-3-(trifluoromethoxy)benzonitrile (example 10A) are suspended in 5 ml of abs. THF and, after addition of 6.78 ml (6.78 mmol) of N″′-(tert-butyl)-N,N′,N″-tris[tris(dimethylamino)-phosphoranylidene]phosphorimide triamide (phosphazene base P4-t-Bu; 1 M in hexane), stirred for 5 min. Then 1.32 g (7.40 mmol) of ethyl trifluoromethanesulfonate are added. After stirring for a further 5 min, the mixture is hydrolyzed with saturated sodium bicarbonate solution and extracted twice with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried with sodium sulfate and then concentrated in a rotary evaporator. The residue is purified by column chromatography (silica gel, mobile phase: cyclohexane/ethyl acetate 3:7). Recrystallization from acetonitrile finally affords 745 mg (29% of theory) of the title compound.

Provenance & Evidence