Potassium Carbonate → 3-[1-(2,6-Dichlorophenyl)ethyl]-5-(1-piperidin-4-yl-1H-pyrazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 5-bromo-3-[1-(2,6-dichlorophenyl)ethyl]-1H-pyrrolo[2,3-b]-pyridine (10.00 mg, 0.027 mmol), 4-[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-piperidine hydrochloride (11.00 mg, 0.035 mmol), potassium carbonate (15.00 mg, 0.11 mmol) in DME (2.0 mL) and H2O (0.40 mL) was added (1,1′-bis-(diphenylphosphino)ferrocene)palladium dichloride (0.84 mg, 0.0011 mmol) under nitrogen atmosphere. The resulting mixture was refluxed at 100° C. for 90 min. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography (eluent: 8% MeOH in DCM) to give desired product. 1H NMR (400 MHz, CD3OD): δ=1.92 (d, J=7.1 Hz, 3H), 1.98-2.21 (m, 4H), 2.76-2.91 (m, 2H), 3.19-3.32 (m, 2H), 4.30-4.44 (m, 1H), 5.27-5.40 (m, 1H), 7.20-7.51 (m, 5H), 7.59 (s, 1H), 7.89 (s, 1H), 8.34 (d, J=2.0 Hz, 1H). MS (ES+): m/z 440.06, 442.06 [MH+]. HPLC: tR=2.46 min (ZQ3, polar—5 min)

Provenance & Evidence