Tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carbamate → 2-(2-aminopyridin-3-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-one

Participants

Reaction Conditions

Reaction Steps

A solution of tert-butyl (3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)carba mate (736 mg, 2.3 mmol), 2-bromo-4H-thieno[2,3-c]pyrrol-6(5H)-one (500 mg, 2.3 mmol) and Pd(PPh3)4 (40 mg, 0.035 mmol) in n-BuOH (5 mL) and 2.0 M Na2CO3 (4.6 mL) was degassed and the resulting reaction mixture was refluxed at 110° C. for 2 h. Upon completion, the reaction was cooled to room temperature, filtered, and washed with MeOH (10 mL) and water (2×10 mL). The solid was dried under high vacuum yielding 2-(2-aminopyridin-3-yl)-4H-thieno[2,3-c]pyrrol-6(5H)-one (383 mg, 72% yield) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 8.40 (br. s., 1H), 8.00 (dd, J=5.0, 1.8 Hz, 1H), 7.52 (dd, J=7.3, 1.8 Hz, 1H), 7.36 (s, 1H), 6.66 (dd, J=7.4, 4.9 Hz, 1H), 5.99 (s, 2H), 4.32 (s, 2H); MS (EI) m/z=232.3 [M+1]+.

Provenance & Evidence