Cesium carbonate → HCID 59511495, compound

Participants

Reaction Conditions

Reaction Steps

A suspension of 1-(7-bromo-4-methoxy-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (100 mg, 0.195 mmol), pyrimidin-4-amine (55.7 mg, 0.586 mmol), Tris(dibenzylideneacetone)dipalladium(0) (8.94 mg, 9.76 μmol), 4,5-Bis(diphenylphosphino)-9,9-dimethylxanthene (11.29 mg, 0.020 mmol) and Cesium carbonate (127 mg, 0.390 mmol) in Dioxane (2 mL) was heated at 115° C. for 4 hours. After cooling to rt, the mixture was diluted with MeOH and filtered. The filtrate was concentrated and purified by prep. HPLC to give 1-(4-methoxy-7-(pyrimidin-4-ylamino)-1H-pyrrolo[2,3-c]pyridin-3-yl)-2-(4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazin-1-yl)ethane-1,2-dione (4.1 mg, 7.79 μmol, 3.99% yield). LCMS: m/e 527.3 (M+H)+, ret time 1.02 min. 1H NMR (500 MHz, MeOD) δ ppm 8.87 (s, 1H) 8.61 (d, J=3.66 Hz, 1H) 8.49 (d, J=6.10 Hz, 1H) 8.42 (s, 1H) 8.03-8.10 (m, 1H) 7.83 (d, J=7.94 Hz, 1H) 7.67 (s, 1H) 7.51-7.56 (m, 2H) 4.02 (s, 3H) 3.83-3.90 (m, 2H) 3.62-3.67 (m, 2H) 3.43-3.56 (m, 4H).

Provenance & Evidence