Potassium Carbonate → HCID 178515524, compound

Participants

Reaction Steps

[4-Benzyloxy-6-(1-triisopropylsilanyl-1H-indol-4-yl)-pyrimidin-2-yl]-pyridin-3-yl-amine. DMF (1 mL) and dioxane (2 mL) were added through a septum to a nitrogen-purged microwave tube containing (4-benzyloxy-6-chloro-pyrimidin-2-yl)-pyridin-3-yl-amine (80 mg, 0.256 mmol), potassium carbonate (71 mg, 0.50 mmol), Pd(PPh3)4 (59 mg, 0.51 mmol), and 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-1-triisopropylsilanyl-1H-indole (153 mg, 0.384 mmol). The mixture was subjected to microwave conditions 100 W/130° C. for 1 hour. SFC/MS analysis showed mostly the desired product. A small amount of product with loss of the TIPS group was seen as well. The reaction mixture was cooled to room temperature and filtered through Celite®. The solvent was concentrated and the crude mixture was purified by a short silica column with 99:1 methylene chloride/MeOH solvent mixture to afford 100 mg of [4-benzyloxy-6-(1-triisopropylsilanyl-1H-indol-4-yl)-pyrimidin-2-yl]-pyridin-3-yl-amine (˜75% pure by SFC/MS). This material was used without further purification.

Provenance & Evidence