Tris(furan-2-yl)phosphane → 2-[4-Methyl-2-(3-pyridyl)thiazol-5-yl]-5,6-dihydrothiopyrano[3,2-d]thiazol-7-one

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Reaction Conditions

Reaction Steps

Tri-n-butyl-[4-methyl-2-(3-pyridyl)thiazol-5-yl]stannane (560 mg, 1.2 mmol, prepared as described previously) and 2-bromo-5,6-dihydrothiopyrano[3,2-d]thiazol-7-one (300 mg, 1.20 mmol), Tris(dibenzylideneacetone)dipalladium(0) (54 mg, 0.06 mmol) and Tri(2-furyl)phosphine (54 mg, 0.23 mmol) were dissolved in 10 ml of dioxane and placed in a steel tube. The mixture were evacuated, flushed with N2 3 times and heated at 100° C. for 18 hours. After cooling to ambient temperature, the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified with chromatography (Ethyl acetate: Petroleum ether=2/1) to give the title compound (83 mg, 20% yield). 1H NMR (400 Mz, CDCl3): δ2.79 (s, 3H), 3.04 (t, 2H), 3.46 (t, 2H), 7.43-7.45 (m, 1H), 8.43 (d, 1H), 8.69 (d, 1H), 9.20 (s, 1H).

Provenance & Evidence