Potassium Iodide → HCID 86681505, compound

Participants

Reaction Steps

37.4 g (114 mmol) of caesium carbonate and 0.91 g, (5.47 mmol) of potassium iodide were added to a solution of 10.7 g (60.1 mmol) of 2-(hydroxyimino)-N-methyl-2-phenylacetamide (81:19 mixture of the Z and E diastereoisomers) and 13.3 g (54.7 mmol) of tert-butyl [6-(chloromethyl)pyridin-2-yl]carbamate in 100 ml of acetonitrile: DMF 75:25. After stirring for 3 h at room temperature, the mixture was concentrated by evaporation in vacuo and the residue was admixed with 250 ml of ethyl acetate. Then, 500 ml of water were added, the phases were separated and the aqueous phase was extracted again with 250 ml of ethyl acetate. The combined organic phases were dried with MgSO4 and concentrated by evaporation in vacuo. This gave 16.8 g (95% purity; 89:11 mixture of Z and E isomers) of tert-butyl {6-[({[2-(methylamino)-2-oxo-1-phenylethylidene]amino}oxy)methyl]pyridin-2-yl}carbamate.

Provenance & Evidence