Cesium carbonate → HCID 44518227, compound

Participants

Reaction Conditions

Reaction Steps

In step 1-4, tris(dibenzylideneacetone) dipalladium (0) (10.8 mg, 0.012 mmol), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (22 mg, 0.047 mmol) and cesium carbonate (77 mg, 0.24 mmol) were added consecutively into a solution of 3-(5-chloro-3H-imidazo[4,5-b]pyridin-3-yl)benzonitrile (30 mg, 0.12 mmol) and 2-(3-fluorophenyl)pyrrolidine (29 mg, 0.18 mmol) in 1,4-dioxane. The mixture was degased under house vacuum, and charged with nitrogen and heated for 18 hours at 100° C. The reaction mixtures was purified using HPLC to afford 3-(5-(2-(3-fluorophenyl)pyrrolidin-1-yl)-3H-imidazo[4,5-b]pyridin-3-yl)benzonitrile (1-4) as a white solid. 1H NMR methanol-d4 δ (ppm) 8.86 (s, 1H), 8.28 (s, 1H), 7.98 (m, 1H), 7.89 (d, 1H), 7.78 (d, 1H), 7.63 (t, 1H), 7.33 (m, 1H), 7.09 (dm, 1H), 6.93 (m, 2H), 6.70 (d, 1H), 5.18 (d, 1H), 3.94 (m, 1H), 3.68 (m, 1H), 2.48 (m, 1H), 2.11 (m, 2), 1.97 (m, 1H); m/z 384 (M+1).

Provenance & Evidence