4-(Tri-n-butylstannyl)pyridine → 2,3-Dichloro-N-[5-(4-pyridinyl)-3-(3-pyridinylmethoxy)-2-pyrazinyl]benzenesulphonamide

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Reaction Steps

[5-Bromo-3-(3-pyridinylmethoxy)-2-pyrazinyl][(2,3-dichlorophenyl)sulphonyl]carbamic acid, 2-methylpropyl ester (Example 136a) (0.11 g), 4-tributylstannanylpyridine (0.067 g) and tetrakis(triphenylphosphine)palladium(0) (0.05 g) in toluene (3 mL) was heated at 95° C. for 16 h. Chromatography on silica gel eluting with ethyl acetate/ethanol mixtures gave the title compound protected with the 2-methylpropylcarbonyl group (0.09 g). The compound was heated at 60° C. in methanol (2 mL) and 1M sodium hydroxide (0.36 mL) for 1 h. The solution was evaporated. Purification was by reverse phase preparative high pressure liquid chromatography. Yield 0.015 g.

Provenance & Evidence