反応 #838492

反応方程式

triphenylphosphine

6-iodoisoquinoline

2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid

potassium carbonate

→

title compound

収率 51.2%

6-[2-(6-Methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl]-isoquinoline

収率 51.2%

溶媒

dioxane

反応条件

後処理

1. 1
   温度Reflux the mixture for 2 h
2. 2
   洗浄wash the resin sequentially with 1 volume dichloromethane, 1 volume methanol, and 1 volume methanol containing 2N ammonia
3. 3
   その他Remove the organic solvents under reduced pressure

実験手順

Dissolve 6-iodoisoquinoline (0.085 g, 0.333 mmol) and 2-(6-methyl-pyridin-2-yl)-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-boronic acid (Preparation 2; 0.077 g, 0.317 mmol) in dioxane (2.5 mL). Add 5M aqueous potassium carbonate (0.667 mL, 3.33 mmol) followed by triphenylphosphine (5.2 g, 0.020 mmol) and tris(dibenzylidineacetone)dipalladium (18 mg, 0.020 mmol). Reflux the mixture for 2 h and cool to room temperature. Load the reaction mixture on to a cartridge containing SCX resin (5 g) and wash the resin sequentially with 1 volume dichloromethane, 1 volume methanol, and 1 volume methanol containing 2N ammonia. Remove the organic solvents under reduced pressure. Chromatograph on 15 g silica gel eluting with 5% methanol in ethyl acetate to provide 0.053 g (48%) of the title compound as a tan solid.

出典