Potassium Carbonate → HCID 44465600, compound

Participants

Reaction Conditions

Reaction Steps

To 2-bromo-1-(4-hydroxy-phenyl)-1H-indole-3-carbonitrile (Example 1) was added 2 eq 3-thiopheneboronic acid, 2.1 eq potassium carbonate and 10 mol % tetrakis(triphenylphosphine) palladium. THF:EtOH:H2O (4:1:0.5) was added and the vial was flushed with nitrogen, sealed and stirred at 100° C. for 48 hours. The reaction mixture was cooled to rt, diluted with H2O, extracted with EtOAc and filtered through silica. The organic phase was evaporated to dryness and the crude product was subjected to reversed phase preparative HPLC. Appropriate fractions were combined, evaporated, and identified by 1H-NMR and LC/MS. Purity was determined by analytical HPLC. ES/MS m/z: 317.9 (M+H), 314.8 (M−H); 1H NMR (acetone-d6, 500 MHz): 7.73 (m, 1H), 7.62 (dd, 1H, J=1.3, 2.9 Hz), 7.54 (dd, 1H, J=2.9, 5.0 Hz), 7.37-7.30 (m, 2H), 7.26 (m, 2H), 7.18 (m, 1H), 7.15 (dd, 1H, J=1.3, 5.0 Hz) and 7.03 (m, 2H).

Provenance & Evidence