Dichloromethane → HCID 68695164, compound

Participants

Reaction Conditions

Reaction Steps

Compounds 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), 3,5-dimethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)isoxazole, 1,1′-Bis(diphenylphosphino)ferrocene palladium (II) chloride complex with dichloromethane (16.06 mg, 0.020 mmol) and Cesium carbonate (127 mg, 0.390 mmol) were combined in Dioxane (2 mL) and Water (0.5 mL). The mixture was heated at 115° C. for 2 hours. After cooling to rt, the mixture was diluted with 10 ml of MeOH and filtered. The filtration was concentrated and purified by HPLC to give 1-(7-(3,5-dimethylisoxazol-4-yl)-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 (56 mg, 0.106 mmol, 54.3% yield). LCMS: m/e 529.3 (M+H)+, ret time 1.03 min. 1H NMR (500 MHz, MeOD) δ ppm 8.65 (s, 1H) 8.62-8.64 (m, J=4.88 Hz, 1H) 8.23 (s, 1H) 8.08-8.13 (m, 1H) 7.84 (d, J=8.24 Hz, 1H) 7.55-7.60 (m, J=6.71, 4.88 Hz, 1H) 4.15 (s, 3H) 3.87-3.90 (m, 2H) 3.66-3.69 (m, 2H) 3.44-3.54 (m, 4H) 2.41 (s, 3H) 2.22 (s, 3H).

Provenance & Evidence