Cesium carbonate → HCID 58197945, compound

Participants

Reaction Conditions

Reaction Steps

A 10 mL microwave tube was charged with a mixture of 6′-bromo-5,6,8,9-tetrahydrospiro[cyclohepta[d]pyridazine-7,2′-inden]-1′(3′H)-one and 6′-bromo-5,7,8,9-tetrahydrospiro[cyclohepta[d]pyridazine-6,2′-inden]-1′(3′H)-one (0.1646 g), obtained as described above, 3-cyanophenylboronic acid (0.2530 g, 1.7 mmol), Cs2CO3 (0.6177 g, 1.9 mmol), 1,4-dioxane (4 mL), water (1 mL), and PdCl2(PPh3)2 (0.0360 g, 0.05 mmol). The tube was heated in a CEM microwave reactor at 110° C. for 30 min. The reaction mixture was diluted with CH2Cl2 and dried over Na2SO4. After the solvent was evaporated under reduced pressure, the residue was purified by reversed-phase HPLC (SunFire™ Prep C18 OBD™ 5 μm 19×50 mm column, 10%→90% MeOH/H2O, 0.1% CF3COOH over 8 min and then 90% MeOH/H2O, 0.1% CF3COOH over 2 min, flow rate 20 mL/min) to afford 0.0281 g of 3-(1′-oxo-1′,3′,5,6,8,9-hexahydrospiro[cyclohepta[d]pyridazine-7,2′-inden]-6′-yl)benzonitrile and 0.0925 g of 3-(1′-oxo-1′,3′,5,7,8,9-hexahydrospiro[cyclohepta[d]pyridazine-6,2′-inden]-6′-yl)benzonitrile.

Provenance & Evidence