2,5-Bis(tri-n-butylstannyl)furan → HCID 178502855, compound

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Reaction Steps

Continuing with Scheme 5, a mixture of 26 (6, mmol), 2,5-bis(tri-n-butylstannyl)furan (3 mmol) and tetrakis(triphenylphosphine)-palladium(0) (150 mg) in dry 1,4-dioxane (20 mL) was heated under nitrogen at reflux (100–110° C.) for 24 h. The solvent was evaporated under reduced pressure, dissolved in methylene chloride, and the solution was passed through celite to remove Pd. The solution was evaporated, the solid was filtered and washed with hexanes to afford 27 (SiO2, hexanes/EtOAc, 1:1), yield 35%, mp 228–230° C. 1H nmr (DMSO-d6); δ 3.80 (s, 6H), 6.31 (s, 4H), 7.34 (s, 2H), 7.98 (d, J=8.4 Hz, 2H), 8.13 (dd, J=8.4, 2.4 Hz, 2H). 8.88 (d, J=2.4 Hz, 2H). 13C nmr; δ 153.5, 148.9, 148.3, 147.0, 134.1, 126.8, 118.1, 112.0, 60.7. MS (m/z, rel.int.); 366 (M+, 100), 335 (25), 319 (30), 288 (40). High resolution mass calcd. for C18H18N6O3: 366.14404. Observed: 366.14012.

Provenance & Evidence