Phthalimide → HCID 86680503, compound

Participants

Reaction Conditions

Reaction Steps

In a reaction flask was combined phthalimide (1.530 g, 10.40 mmol), triphenylphosphine (2.73 g, 10.40 mmol), (R)-1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)-ethanol (2.15 g, 8.66 mmol) and tetrahydrofuran (57.8 mL). The reaction was cooled to 0° C. and diisopropyl azodicarboxylate (2.043 mL, 10.40 mmol) was added dropwise. The reaction was removed from the ice bath and allowed to warm to rt and stir overnight. The reaction was diluted with ethyl acetate and washed with NaHCO3 and brine. The organic layer was dried over MgSO4, filtered and concentrated. Purification using 5-10% ethyl acetate in hexanes afforded (S)-2-(1-(2,6-dichlorothieno[2,3-b]pyridin-5-yl)ethyl)isoindoline-1,3-dione. 1H NMR (400 MHz, CDCl3) δ 8.37 (s, 1H), 7.82 (m, 2H), 7.73*m, 2H), 7.18 (s, 1H), 5.90 (q, 7.3 Hz, 1H), 1.90 (d, J=7.2 Hz, 3H) ppm.

Provenance & Evidence