Tributylvinyltin → HCID 68109354, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of tert-butyl 8-(phenylsulfonyl)-6-(((trifluoromethyl)sulfonyl)oxy)-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (200 mg, 0.45 mmol), tributyl(vinyl)stannane (0.11 mL, 0.48 mmol), lithium chloride (45 mg, 1.34 mmol) and palladium tetrakis(triphenylphosphine) (8 mg, 0.01 mmol) was suspended in anhydrous 1,4-dioxane (5 mL). The flask was purged with argon, sealed, and heated to 100° C. for 3 h. The reaction mixture was cooled to ambient temperature, diluted with water, and extracted with ethyl acetate. The organic extract was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography (SiO2, 9:1 hexanes/ethyl acetate) to give tert-butyl 8-(phenylsulfonyl)-6-vinyl-3,4-dihydrobenzofuro[3,2-c]pyridine-2(1H)-carboxylate (120 mg, 77%) as a white solid: 1H NMR (CDCl3, 300 MHz) δ 8.00-7.90 (m, 3H), 7.86 (s, 1H), 7.61-7.45 (m, 3H), 7.00-6.84 (m, 1H), 6.23 (d, J=17.4 Hz, 1H), 5.60 (d, J=17.4 Hz, 1H), 4.57 (s, 2H), 3.84 (t, J=5.7 Hz, 2H), 2.88 (br s, 2H), 1.51 (s, 9H).

Provenance & Evidence