Potassium Carbonate → HCID 57960851, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred mixture of 3-cyclobutyl-1-iodoimidazo[1,5-a]pyrazin-8-amine (100.00 mg, 0.318 mmol), potassium carbonate (154.0 mg, 1.11 mmol) in DME (3.0 mL) and H2O (0.70 mL) was added 4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3,6-dihydro-2H-pyridine-1-carboxylic acid tert-butyl ester (118.1 mg, 0.38 mmol). The solution was bubbled with nitrogen for 5 min. Then Pd(PPh3)4 (18 mg, 0.016 mmol) was added and the resulting mixture was refluxed at 100° C. for 30 min. The solvent was then removed under reduced pressure and the resulting residue was purified by a flash chromatography (2% MeOH in DCM). 1H NMR (400 MHz, MeOD) δ 1.53 (s, 9H), 1.95-2.07 (m, 1H), 2.14-2.28 (m, 1H), 2.44-2.54 (m, 4H), 2.62-2.71 (m, 2H), 3.73 (t, J=5.68 Hz, 2H), 3.87-3.98 (m, 1H), 4.12-421 (m, 2H), 5.94-6.00 (m, 1H), 6.96 (d, J=5.20 Hz, 1H), 7.33 (d, J=5.20 Hz, 1H). MS (ES+): m/z: 369.94, [MH+], HPLC: tR=2.33 min (OpenLynx, polar—5 min).

Provenance & Evidence