E-2-(3,3-DIMETHYLBUTENYL)BORONIC ACID PINACOL ESTER

Conditions: temp:130.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: A mixture of (S)-3-chloro-7-(pyrimidin-5-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine (0.967 g, 2.64 mmol), trans-(3,3-dimethylbutenyl)boronic acid pinacol ester (1.389 g, 6.61 mmol), AmPhos (0.094 g, 0.132 mmol), and potassium phosphate hydrate (1.218 g, 5.29 mmol) in 10 mL dioxane/water (1:1) was heated in the microwave at 130° C. for 1 h. After cooling to rt, the reaction was concentrated and the residue purified by silica gel chromatography using 0-5% MeOH/DCM to give (S,E)-3-(3,3-dimethylbut-1-enyl)-7-(pyrimidin-5-yl)-5′H-spiro[chromeno[2,3-c]pyridine-5,4′-oxazol]-2′-amine. Found MS: MH+=414. After cooling to rt the reaction was concentrated the residue purified by silica gel chromatography