N,N'-Dimethylethylenediamine → 2-(4-Chloro-phenyl)-6-[6-((3R,3'R)-3-fluoro-[1,3']bipyrrolidinyl-1'-yl)-pyridin-3-yl]-6H-thieno[2,3-c]pyridin-7-one

Participants

Reaction Conditions

Reaction Steps

Degass a mixture of 2-(4-chloro-phenyl)-6H-thieno[2,3-c]pyridin-7-one (458 mg, 1.75 mmol), (3R,3′R)-1′-(5-bromo-pyridin-2-yl)-3-fluoro-[1,3′]bipyrrolidinyl (550 mg, 1.75 mmol) and cesium carbonate (1.14 g, 3.50 mmol) in 1,4-dioxane (20 mL). Add copper (I) iodide (133 mg, 700 μmol) and sym-dimethylethylene diamine (99 μL, 928 μmol). Heat the mixture at 100° C. overnight. Add to the cooled mixture concentrated NH4OH (5 mL). After 10 min, pour the mixture into water (20 mL). Filter the resulting solid and rinse with water (2×), followed by rinsing with Et2O (2×). Purify using chromatography (0 to 5% MeOH/CH2Cl2) to afford 610 mg (71%) of the title compound. 1H NMR (400 MHz, CDCl3) δ: 1.95 (m, 1H), 2.24 (m, 3H), 3.59 (m, 8H), 5.18 (d, 1H), 5.40 (brs, 1H), 6.44 (d, 1H), 6.65 (d, 1H), 7.22 (d, 1H), 7.38 (t, 3H), 7.60 (m, 3H), 8.13 (s, 1H).

Provenance & Evidence