甲基3,5-二甲基-4-(4,4,5,5-四甲基-1,3,2-二氧硼烷-2-基)苯甲酸甲酯

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Step A, 2.79 g, 7.20 mmol), 1,1′-bis(di-tert-butylphoshino)ferrocene palladium dichloride (0.391 g, 0.600 mmol) and 5-bromo-2-methoxypyridine (0.776 mL, 6 mmol) were mixed in a reaction flask which was then evacuated and charged with nitrogen three times. Added 1,4-dioxane (30.0 mL) and 3.0M aqueous potassium carbonate (6.00 mL, 18.00 mmol), evacuated and charged with nitrogen (3×), then stirred overnight at 80° C. The reaction was then partitioned between ethyl acetate and water. After a second water wash, the organic was dried over sodium sulfate, filtered and evaporated. The crude was purified by silica gel chromatography, eluting with 10 column volumes of 4% ethyl acetate/hexanes followed by a gradient of 4-10% ethyl acetate/hexanes over 10 column volumes to give the title compound. 1H NMR (CDCl3, 500 MHz) δ7.94 (d, 1H), 67.79 (s, 2H), 67.36 (dd, 1H), 66.84 (d, 1H), 64.00 (s, 3H), 63.93 (s, 3H), 62.09 (s, 6H). was then evacuated charged with nitrogen three times charged with nitrogen (3×) The reaction was then partitioned between ethyl acetate and water After a second water wash the organic was dried over sodium sulfate filtered evaporated The crude was purified by silica gel chromatography eluting with 10 column volumes of 4% ethyl acetate/hexanes

反应条件: temp:80.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: Methyl 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate (Step A, 2.79 g, 7.20 mmol), 1,1′-bis(di-tert-butylphoshino)ferrocene palladium dichloride (0.391 g, 0.600 mmol) and 5-bromo-2-methoxypyridine (0.776 mL, 6 mmol) were mixed in a reaction flask which was then evacuated and charged with nitrogen three times. Added 1,4-dioxane (30.0 mL) and 3.0M aqueous potassium carbonate (6.00 mL, 18.00 mmol), evacuated and charged with nitrogen (3×), then stirred overnight at 80° C. The reaction was then partitioned between ethyl acetate and water. After a second water wash, the organic was dried over sodium sulfate, filtered and evaporated. The crude was purified by silica gel chromatography, eluting with 10 column volumes of 4% ethyl acetate/hexanes followed by a gradient of 4-10% ethyl acetate/hexanes over 10 column volumes to give the title compound. 1H NMR (CDCl3, 500 MHz) δ7.94 (d, 1H), 67.79 (s, 2H), 67.36 (dd, 1H), 66.84 (d, 1H), 64.00 (s, 3H), 63.93 (s, 3H), 62.09 (s, 6H). was then evacuated charged with nitrogen three times charged with nitrogen (3×) The reaction was then partitioned between ethyl acetate and water After a second water wash the organic was dried over sodium sulfate filtered evaporated The crude was purified by silica gel chromatography eluting with 10 column volumes of 4% ethyl acetate/hexanes