2-Bromopyridine → N-{[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-yl]methyl}pyridin-2-amine

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Reaction Steps

1-[4-(4-{[tert-butyl(dimethyl)silyl]oxy}phenyl)tetrahydro-2H-pyran-4-yl]methanamine (3.65 g, 11.4 mmol), 2-bromopyridine (910 μl, 9.48 mmol), tris(dibenzylideneacetone)dipalladium(0) (471 mg, 0.455 mmol), 2,2′-bis(diphenylphosphino)1,1′-binaphyl (567 mg, 0.910 mmol) and sodium tert-butoxide (1.29 g, 13.0 mmol) were stirred in toluene (50 ml) at 70° C. under nitrogen for 24 hours. The toluene was removed in vacuo and the residue partitioned between dichloromethane (50 ml) and saturated sodium bicarbonate solution (50 ml). The organic layer was separated and dried over sodium sulphate, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel eluting with ether:pentane (80:20 by volume) to provide the title compound (2.10 g, 46%) as a yellow solid. LRMS APCI+ m/z 399 [MH]+.

Provenance & Evidence