Cesium carbonate → HCID 67383534, compound

Participants

Reaction Conditions

Reaction Steps

A vial charged with allylchloro[1,3-bis(2,6-di-1-propylphenyl)-4,5-dihydroimidazol-2-ylidene]palladium(ii) (0.072 g, 0.126 mmol), cesium carbonate (1.10 g, 3.36 mmol), potassium tert-butoxymethyltrifluoroborate (0.49 g, 2.52 mmol), and (S)-7-bromo-8-fluoro-3-iodo-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.40 g, 0.84 mmol, prepared as described in Method BB24) was treated with 3 mL dioxane and 0.3 mL water, was capped under argon, and was heated to 130° C. overnight. The reaction mixture was diluted with EtOAc, dried over MgSO4 and concentrated. Purification of the crude residue by column chromatography gave (S)-7-bromo-3-(tert-butoxymethyl)-8-fluoro-5′H-spiro[chromeno[2,3-b]pyridine-5,4′-oxazol]-2′-amine (0.073 g, 0.167 mmol, 19.91% yield) with impurities.

Provenance & Evidence