Tert-butyl 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1,2,3,6-tetrahydropyridine-1-carboxylate → HCID 67607456, compound

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Reaction Steps

100 mg (0.29 mmol) of 2-bromo-6-(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)pyridine and 135 mg (0.44 mmol) of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester are dissolved in 2 ml of 2M sodium carbonate solution and in 2 ml of dimethoxyethane. The reaction mixture is degassed a number of times, 34 mg (0.03 mmol) of tetrakis(triphenylphosphine)palladium are added under nitrogen atmosphere, and the mixture is irradiated in the microwave for 30 min, subsequently evaporated, and saturated sodium hydrogencarbonate solution is added. This mixture is extracted three times with ethyl acetate, the combined organic phases are dried over Na2SO4 and evaporated. The crude product is purified by column chromatography on silica gel.

Provenance & Evidence