Cesium carbonate → HCID 72550880, compound

Participants

Reaction Conditions

Reaction Steps

2′-amino-2-bromo-1′-methyl-6,7-dihydro-5H-spiro[benzo[b]thiophene-4,4′-imidazol]-5′(1′H)-one (0.127 g, 0.4 mmol), 3-cyanophenyl boronic acid (59 mg, 0.4 mmol) and Pd(dppf)Cl2 (33 mg, 0.04 mmol), were suspended in DMF (1.5 mL). Cs2CO3 (0.35 mL, 3.7 M aq. solution, 1.29 mmol) was added and the solution was degassed under a stream of nitrogen for 10 min. The mixture was heated at 90° C. for 2 hr. The reaction was cooled and solvent was removed in vacuo. The crude residue was purified using preparative HPLC to give the title compound as off-white solid (14 mg, 11%). 1H NMR δ (ppm)(DMSO-d6): 8.11 (1H, s), 7.86 (1H, d, J=8.18 Hz), 7.71 (1H, d, J=7.72 Hz), 7.57 (1H, t, J=7.85 Hz), 7.14 (1H, s), 6.41 (2H, br s), 3.02 (3H, s), 2.84-2.76 (2H, m), 2.11 (1H, d, J=13.56 Hz), 1.91 (2H, s), 1.70 (1H, s). HPLC (Method c) Rt 9.2 (min) m/z 337 (MH+).

Provenance & Evidence