Potassium Carbonate → 3-[1-(2,6-Dichloro-3-fluorophenyl)ethyl]-5-(1-methyl-1H-imidazol-4-yl)-1H-pyrrolo[2,3-b]pyridine

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 3-[1-(2,6-dichloro-3-fluorophenyl)ethyl]-5-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrrolo[2,3-b]pyridine (10.0 mg, 0.0229 mmol), 4-iodo-1-methyl-1H-imidazole (7.17 mg, 0.0344 mmol), potassium carbonate (9.53 mg, 0.0689 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: 2% MeOH in DCM) to give desired product. 1H NMR (400 MHz, CD3OD): δ=1.88 (d, J=7.1 Hz, 3 H), 3.75 (s, 3 H), 5.30 (q, J=6.8 Hz, 1 H), 7.12-7.18 (m, 1 H), 7.22 (d, J=1.5 Hz, 1 H), 7.33 (d, J=1.3 Hz, 1 H), 7.39 (br. s., 1 H), 7.62 (s, 1 H), 7.67 (d, J=2.0 Hz, 1 H), 8.48 (d, J=2.0 Hz, 1H). MS (ES+): m/z 389.05 [MH+]. HPLC: tR=2.54 min (ZQ3, polar—5 min).

Provenance & Evidence