Potassium Carbonate → HCID 58266442, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 1-ethyl-4-methylene-piperidine (540 mg, 4.32 mmol) and 9-borabicyclo[3.3.1]nonane (0.5M in THF, 8.0 mL, 4.0 mmol) was heated at 65° C. for 3.5 h. The resultant cooled solution was then added portionwise to a degassed suspension of 9-benzenesulfonyl-5-bromo-9H-dipyrido[2,3-b;4′,3′-d]pyrrole-6-carbonitrile (420 mg, 1 mmol), bis(diphenylphosphino)ferrocene dichloropalladium(II) (90 mg, 0.11 mmol) and potassium carbonate (180 mg, 1.3 mmol) in water (1 mL) and dimethylformamide (10 mL). The resultant orange solution was heated at 65° C. for 2 h then allowed to cool to ambient temperature and partitioned between dichloromethane (20 mL) and a saturated aqueous solution of sodium chloride (15 mL). The aqueous phase was extracted with dichloromethane (3×10 mL) and the combined organic phase was washed with a saturated aqueous solution of sodium chloride (20 mL), dried over magnesium sulfate and concentrated in vacuo. The resultant residue was purified by flash chromatography (silica, 10 g column, Si-SPE, 0-20% MeOH in DCM) to afford the title compound (200 mg, 43%). 1H NMR (CDCl3, 400 MHz): 9.81 (s, 1H), 8.76 (dd, J=4.8, 1.5 Hz, 1H), 8.66 (d, J=8.0 Hz, 1H), 8.29-8.24 (m, 2H), 7.66-7.60 (m, 1H), 7.58-7.48 (m, 3H), 3.41 (d, J=7.2 Hz, 2H), 2.89 (q, J=7.3 Hz, 2H), 2.56-2.44 (m, 2H), 2.33-2.08 (m, 3H), 1.94-1.74 (m, 4H), 1.35 (t, J=7.3 Hz, 3H). LCMS (Method G): RT=3.01 min, M+H+=460.

Provenance & Evidence