Potassium Carbonate → HCID 59276285, compound

Participants

Reaction Conditions

Reaction Steps

tert-Butyl 3,3-dimethyl-2-oxo-6-(5-(tetrahydro-2H-pyran-4-carbonyl)-[1,2,4]triazolo[1,5-a]pyridin-2-ylamino)indoline-1-carboxylate. A mixture of tris(dibenzylideneacetone)dipalladium(0) (0.050 g, 0.054 mmol) and 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (0.063 g, 0.109 mmol) in 1,4-dioxane (2 mL) was heated briefly with a heat gun until very hot and then added to tert-butyl 6-amino-3,3-dimethyl-2-oxoindoline-1-carboxylate (0.150 g, 0.543 mmol), (2-bromo-[1,2,4]triazolo[1,5-a]pyridin-5-yl)(tetrahydro-2H-pyran-4-yl)methanone (0.168 g, 0.543 mmol) and finely ground potassium carbonate (0.308 g, 2.226 mmol) in a sealable vessel with a stirbar. Nitrogen was blown in to blow out air. The resulting mixture was sealed, stirred vigorously, and heated at 100° C. for 1.5 h. After cooling to room temperature the reaction mixture was diluted with ethyl acetate and water with vigorous stirring. The resulting mixture was filtered through a syringe filter and the filter cake washed with ethyl acetate. The layers of the filtrate were separated in a reparatory funnel and the organics were concentrated on a rotary evaporator. The residue was taken up in dichloromethane and purified using flash chromatography (Biotage) (20-80% ethyl acetate in hexane) to give the desired product (0.183 g, 0.362 mmol, 67% yield) as a yellow solid. MS (ESI) m/z 506.2 [M+1]+.

Provenance & Evidence