2-(Tributylstannyl)pyridine → HCID 66633234, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-(1-(6-chlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (300 mg, 0.875 mmol), 2-(tributylstannyl)pyridine (340 μL, 1.05 mmol, 1.2 eq) and tetrakis(triphenylphosphine)palladium(0) (101 mg, 0.0875 mmol, 0.1 eq) was dissolved in 10 mL of dioxane under nitrogen. The reaction was heated to 100° C. for 2 days, cooled to rt and concentrated in vacuo. Purification by column chromatography using ethyl acetate/hexanes afforded 2-(1-(6-(pyridin-2-yl)-thieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. LC/MS (M+1, found=386.0). 1H NMR (400 MHz, CDCl3) δ 8.69 (s, 1H), 8.66 (ddd, J=4.9, 1.6, 0.8 Hz, 1H), 7.76 (td, J=7.8, 1.8 Hz, 1H), 7.73-7.62, series of m, 5H), 7.57 (d, J=5.9 Hz, 1H), 7.36 (d, J=5.9 Hz, 1H), 7.31 (ddd, J=7.2, 4.7, 1.4 Hz, 1H), 6.33 (q, J=7.2 Hz, 1H), 1.99 (d, J=7.2 Hz, 3H) ppm.

Provenance & Evidence