1-(3-碘苯基)-N,N-二甲基甲胺

反应条件: temp:100.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: In a 250 ml round bottom flask were charged 4-[6-chloro-1-(tetrahydro-pyran-2-yl)-3-vinyl-1H-pyrazolo[3,4-b]pyridine-4-carbonyl]-piperazine-1-carboxylic acid tert-butyl ester (1.2 g, 2.52 mmol), (3-iodo-benzyl)-dimethyl-amine (1.64 g, 6.3 mmol), tetrabutylammonium bromide (0.32 g, 1 mmol), sodium hydrogen carbonate (0.53 g, 6.3 mmol) and anhydrous dimethylformamide (42 ml). The mixture was degassed during 10 minutes using argon, palladium acetate (0.05 g, 0.25 mmol) was then added. The resulting solution was heated at 100° C. under argon overnight. Dimethylformamide was eliminated under vacuum, dichloromethane and water were added to the residue, after extraction the organic layer was dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give the crude product. Further purification on a silica gel column chromatography using a gradient of methanol (0-5%) in dichloromethane afforded the title compound as brown solid (0.44 g, 29%). The mixture was degassed during 10 minutes was then added were added to the residue after extraction the organic layer was dried over anhydrous sodium sulfate filtered concentrated under reduced pressure to give the crude product Further purification on a silica gel column chromatography

反应条件: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

实验步骤: To a cold (0° C.) solution of 3-iodo-benzaldehyde (3 g, 12.9 mmol) in anhydrous dichloromethane (130 ml) were added acetic acid (1.9 ml) and N,N-dimethylacetamide. The yellow solution is stirred 10 minutes at 0° C. and sodium triacetoxyborohydride (6.85 g, 32.33 mmoles) is added by portions. The resulting mixture is stirred at room temperature for 90 minutes and evaporated to dryness under reduced pressure. Ethyl acetate and a saturated aqueous hydrogen carbonate solution were added to the residue and the two layers were separated The organic phase was washed with water, dried over anhydrous sodium sulfate, filtered and concentrated under vacuum to yield (3-iodo-benzyl)-dimethyl-amine (3.05 g, 90%) as a brown oil. The resulting mixture is stirred at room temperature for 90 minutes evaporated to dryness under reduced pressure Ethyl acetate and a saturated aqueous hydrogen carbonate solution were added to the residue the two layers were separated The organic phase was washed with water dried over anhydrous sodium sulfate filtered concentrated under vacuum