Methanol → HCID 89815345, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1 h-pyrrolo[2,3-b]pyridine (0.477 g, 1.955 mmol), 4-((S)-5,5-dimethyl-2-oxo-4-phenyloxazolidin-3-yl)cyclohex-1-en-1-yl trifluoromethanesulfonate (0.82 g, 1.955 mmol) and 2.0 M sodium carbonate (4.89 mL) in dioxane (6.52 mL) was flushed with nitrogen. Tetrakis(triphenylphosphine)palladium(0) (0.226 g, 0.196 mmol) was added and the mixture was stirred at 100° C. overnight. The reaction mixture was diluted with CH2Cl2 and extracted with CH2Cl2. The combined organic layers were concentrated. The material thus obtained was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% 1M NH3.MeOH in CH2Cl2, to provide (4S)-3-(4-(1H-pyrrolo[2,3-b]pyridin-5-yl)cyclohex-3-en-1-yl)-5,5-dimethyl-4-phenyloxazolidin-2-one (0.76 g, 1.961 mmol, 100% yield) as light-yellow solid.

Provenance & Evidence