Ethanol → 3-(4-Pyrazinylphenyl)-2-propvn-1-ol

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Reaction Steps

Chloropyrazine (0.78 mL, 8.73 mmol), 1 M aq. Na2CO3 (10 mL), and ethanol (5 mL) were successively added to a mixture of [1,4-bis(diphenylphosphino)butane]palladium(II) dichloride (0.30 g, 0.50 mmol) and [4-(3-hydroxy-1-propynyl)phenyl]boronic acid (1.85 g, 10.51 mmol, prepared as described in Reference Example 235) in toluene (20 mL) and the resulting mixture was heated to reflux for 3 h. The cooled reaction mixture was diluted with ethyl acetate (50 mL) and the organic layer was separated, washed with brine (50 mL), dried (MgSO4) and concentrated. Purification by chromatography (SiO2, 97:3 dichloromethane/methanol) followed by a second chromatography (SiO2, 1:1 hexane/ethyl acetate) provided 1.22 g (66%) of the title compound as a colorless solid. MS 211 (M+H)+.

Provenance & Evidence