Tetrahydrofuran → HCID 25120535, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[(3-hydroxypropyl)amino]-7-(trifluoromethyl)imidazo[1,2-a]quinoxaline-1-carbaldehyde (35 mg, 0.10 mmol) in anhydrous tetrahydrofuran (190 μL) under Argon were added titanium(IV) isopropoxide (50 μL, 0.17 mmol) and N-methylurea (9 mg, 0.11 mmol). After 5 h at room temperature, sodium borohydride (2.2 mg, 0.05 mmol) was added at 0° C. and the solution was stirred at 35° C. overnight. The mixture was allowed to cool to room temperature, quenched with water (formation of a precipitate) and concentrated. The residue was triturated in ethyl acetate and water, filtrated and rinsed with ethyl acetate and water. The filtrate was washed with a saturated aqueous solution of ammonium chloride and extracted twice with ethyl acetate. The combined organic layers were dried over sodium sulfate, filtered and evaporated. The crude product was purified by preparative TLC (silica gel, dichloromethane/methanol 9/1) to afford the title compound (27 mg, 69%) as a pale yellow solid.

Provenance & Evidence