2-(Tributylstannyl)pyridine → HCID 66633726, compound

Participants

Reaction Conditions

Reaction Steps

In a reaction vessel was combined 2-(1,1,1-tributylstannyl)pyridine (0.124 ml, 0.370 mmol), tetrakis triphenylphosphine(0) (35.6 mg, 0.031 mmol), (S)-2-(1-(6-chloro-2-methylthieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione (110 mg, 0.308 mmol) in dioxane (3 mL). The reaction was heated to 100° C. for 2 d, cooled to rt, and diluted with ethyl acetate. The organic phase was washed with NaHCO3 and brine, dried over MgSO4, filtered and concentrated. Purification by column chromatography afforded (S)-2-(1-(2-methyl-6-(pyridin-2-yl)thieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. 1H NMR (400 MHz, CDCl3) δ 8.64 (ddd, J=4.7, 1.8, 0.8 Hz, 1H), 7.72 (td J=7.8, 2.0 Hz, 1H), 7.67 (m, 3H), 7.62 (m, 2H), 7.29 (ddd, J=7.4, 4.9, 1.6 Hz, 1H), 6.98 (q, J=1.4 Hz, 1H), 6.30 (q, J=7.0 Hz, 1H), 2.60 (d, J=1.2 Hz, 3H), 1.97 (d, J=7.2 Hz, 3H) ppm.

Provenance & Evidence