Water → HCID 57475530, compound

Participants

Reaction Conditions

Reaction Steps

1-Bromo-7,8-dimethoxy-3-methyl-3H-pyrazolo[3,4-c]quinoline (30 mg, 93 μmol) is dissolved in dioxane (1.0 ml) under argon. KOH (5.2 mg, 93 μmol), tert-butyl 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]piperazine-1-carboxylate (83 mg, 214 μmol), trans-bis(tricyclohexylphosphine)palladium(II) dichloride (10.4 mg, 14 μmol) and water (50 μl) are subsequently added. The reaction suspension is subsequently heated at 110° C. (microwave) for 90 min. The mixture is subsequently poured into water, stirred for 15 min, and the precipitate obtained is filtered off with suction. The filter residue is then treated in formic acid (2.5 ml) at room temperature for 18 h, subsequently diluted with water and extracted twice with ethyl acetate. The combined organic phases are washed with water, dried over Na2SO4, filtered with suction and evaporated to dryness in vacuo. The residue is purified by chromatography (pHPLC, solvent gradient water/1-30% by vol. of acetonitrile, 0.1% by vol. of formic acid), and the product fractions are freeze-dried, giving 7,8-dimethoxy-3-methyl-1-(4-piperazin-1-yl)phenyl)-3H-pyrazolo[3,4-c]quinoline (22 mg, 55 μmol) as a solid. MS: 404.1 (M+H+). TLC (HPTLC): Rf=0.19 (methanol/Hünig's base 99:1, parts by volume).

Provenance & Evidence