Methanol → HCID 59596293, compound

Participants

Reaction Steps

Titanium (IV) ethoxide (1M in tetrahydrofuran, 10.2 mL, 10.2 mmol) was added to a solution of 2-(2,6-dichloroisonicotinoyl)benzonitrile (Scheme #19, A, 1.0 g, 3.3 mmol) in tetrahydrofuran (5 mL) at room temperature. After 5 minutes 2-methyl-propanesulfinamide (0.48 g, 3.96 mmol) was added and the reaction mixture was refluxed over night. Additional amounts of titanium (IV) ethoxide (1M in tetrahydrofuran, 3.0 mL, 3.0 mmol) and 2-methyl-propanesulfinamide (0.2 g, 1.6 mmol) were added and the reaction mixture was refluxed for 5 h. After cooled to room temperature methanol (5 mL) and saturated aqueous sodium hydrogen carbonate (0.1 mL) added to the reaction mixture. A precipitation occurred and the crude was filtered through a pad of sodium sulfate before evaporation. Purification by flash chromatography using a stepwise gradient of ethylacetate in heptane afforded the title compound in 44% yield. 1H NMR (CDCl3) δ 7.85-7.78 (m, 1 H), 7.78-7.70 (m, 1 H), 7.68-7.61 (m, 1 H), 7.44-7.35 (m, 1 H), 7.32 (s, 2 H), 1.38 (s, 9 H). MS (API) m/z 380 [M+1]+.

Provenance & Evidence