Hexane → HCID 16118693, compound

Participants

Reaction Steps

To a solution of (2-chloro-[1,7]naphthyridin-8-yl)-(4-methyl-thiazol-2-yl)-amine (0.055 g, 0.20 mmol) in 2 ml dry tetrahydrofuran (purged with argon) were subsequently added tetrakis(triphenylphosphine)palladium (0.011 g, 0.0095 mmol) and a 1.0 M solution of diethylzinc in n-hexane (0.4 ml, 0.4 mmol). The reaction mixture was heated at reflux for 1 h. Cooling to room temperature was followed by quenching with saturated aqueous ammonium chloride solution at 0-5° C. The aquous layer was basified to pH 12 with 1 M aqueous sodium hydroxide solution and extracted with three portions of methyl-tert.-butyl ether. The combined organic layers were washed with brine, dried over sodium sulfate and concentrated to dryness. Flash-chromatography gave the title compound (0.015 g, 28%) as light yellow solid, MS m/e (%): 271 (M+H+, 100).

Provenance & Evidence