Potassium Carbonate → 10-(2,2-Difluoro-benzo[1,3]dioxol-5-yl)-1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one

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Reaction Conditions

Reaction Steps

To a mixture of 1,4-dioxa-10-aza-dispiro[4.2.4.2]tetradecan-9-one (262 mg, 1.24 mmol, obtained in example 133, step 3), potassium carbonate (790 mg, 3.72 mmol) and cuprous iodide (354 mg, 1.86 mmol) was added a solution of 5-bromo-2,2-difluoro-benzo[1,3]dioxole (588 mg, 2.48 mmol) in 5 ml toluene under argon. The solution was then degassed by bubbling argon through the mixture for 2 mins after which N—N′-dimethylethylenediamine (266 uL, 2.48 mmol) was added. The sealed tube was closed and the mixture was heated to 110° C. overnight. The reaction mixture was then cooled to room temperature and filtered through a short pad of Celite® using ethyl acetate to wash the mixture through. The solution was then concentrated in vacuo to give a residue which was purified by flash column chromatography (3:7 ethyl acetate heptane) to give the title compound as white solid (350 mg, 75%). MS (m/e): 368.0 [MH+].

Provenance & Evidence