Sodium hydride → HCID 66995379, compound

Participants

Reaction Steps

Sodium hydride (17.46 mg, 0.437 mmol) was added in a single portion to a solution of 6-bromo-3-(1H-pyrazol-4-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-indazole (101 mg, 0.257 mmol) (prepared by substituting 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole for 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole in Example 1C) in DMF (10 ml) at room temperature under argon. The resulting bubbling solution was stirred for 20 minutes, then treated with 1-(2-chloroethyl)pyrrolidine (51.5 mg, 0.385 mmol) which was dissolved in 0.5 ml DMF and added dropwise via pipette. The resulting mixture was stirred at 70° C. for 3 hours, allowed to cool, and partitioned between ethyl acetate and water. The organic extract was washed with brine, dried with MgSO4, and filtered. The filtrate was concentrated and the residue was purified via silica gel chromatography eluting with 3 to 5% CH2Cl2/CH3OH to give the title compound.

Provenance & Evidence