Ethyl Acetate → HCID 70496154, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(5-bromo-pyridin-3-yl)-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (1.0 g, 2.57 mmol), 4-tert-butylbenzeneboronic acid (0.7 g, 3.86 mmol), tetra(triphenylphosphine)palladium (150 mg, 0.13 mmol) and cesium carbonate (1.7 g, 5.14 mmol) in dimethyl formamide (10 mL) was heated for 3 h at 120° C. After coiling to room temperature, the mixture was treated with ethyl acetate (50 mL) and washed with water (20 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated in vacuo. Purification on flash silica gel chromatography (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company) (10% ethyl acetate/hexanes) to afford 2-[5-(4-tert-butyl-phenyl)-pyridin-3-yl]-4,4-dimethyl-1,2,3,4-tetrahydro-quinoline-6-carboxylic acid ethyl ester (0.8 g, 70%) as a white solid: MS (ESI) M+1=443.3.

Provenance & Evidence