Lithium Hexamethyldisilazide → HCID 90110410, compound

Participants

Reaction Conditions

Reaction Steps

Added N-(2,4-dimethoxybenzyl)-6-fluoropyridin-2-amine (1.0 g, 3.87 mmol) to THF (19 mL) and cooled to −78° C. Added LHMDS (6.5 mL, 6.45 mmol), warmed to RT, stirred for 30 min, and cooled back to −78° C. Following addition of LHMDS, solution turned clear and pink in color. After warming to RT, solution became clear, yellow. At −78° C., added 6-methyl-1H-indazole-5-sulfonyl chloride (4-4, 594.8 mg, 2.58 mmol) in THF (6.5 mL) at −78° C. via syringe followed by THF rinse. Solution remained yellow in color. Allowed reaction flask to remain in bath and gradually warm to RT overnight. Following this duration, quenched with 40 mL saturated NH4Cl, diluted with 20 mL EtOAc. Separated layers, back-extracted aqueous with 3×10 mL EtOAc. Dried organics over Na2SO4, filtered, concentrated to give an orange oil. Purified by normal-phase ISCO (40 g column, 0-50% EtOAc:Hex) to give 4-5 as a white solid.

Provenance & Evidence