Cesium carbonate → HCID 86610749, compound

Participants

Reaction Conditions

Reaction Steps

Add tetrakis(triphenylphosphine)palladium (0.816 g, 0.706 mmol) to a degassed mixture of phenylboronic acid (0.1.72 g, 14.1 mmol), cesium carbonate (9.20 g, 3.5928.2 mmol), and 7-bromo-isoquinoline-5-sulfonic acid (2-{[bis-(4-methoxy-phenyl)-methyl]-amino}-ethyl)-amide (3.93 g, 7.06 mmol) in toluene (75.0 mL) and water (100.0 mL). Warm to 100° C. for 2 hours, and cool to room temperature. Dilute with toluene (100 mL), separate layers, wash sequentially with water and brine, then dry with anhydrous MgSO4, filter and evaporate. Apply the residue to a cation exchange cartridge, wash the cartridge with methanol, and then elute with 2M methanolic ammonia. Evaporation affords the title compound (2.25 g, 58%). 1H NMR (DMSO): δ9.56 (s, 1H), 8.78(d, J=1.8 Hz, 1H), 8.70(d, J=6.2 Hz, 1H), 8.75(d, J=2.0 Hz, 1H), 8.45 (d, J=6.2 Hz, 1H), 7.91(d of t J1=1.3 Hz, J=7.0 Hz, 2H), 7.62(t of t, J1=1.7 Hz, J2=7.4 Hz, 2H), 7.53 (t of t, J1=1.3 Hz, J2=7.4 Hz, 1H), 7.04 (d of t, J1=1.7 Hz, J2=8.8 Hz, 4H), 6.72 (d of t, J1=1.7 Hz, J2=8.8 Hz, 4H), 4.44 (s, 1H), 3.68(s, 6H), 3.01 (t, J=6.1 Hz, 2H), 2.35 (t, J=5.9 Hz, 2H). LCMS: m/z 554 (M+H)+, 552(M−H).

Provenance & Evidence