Sodium Carbonate → HCID 178420009, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of DMF (3 mL) and 2M Na2CO3 (0.75 mL) was purged with nitrogen for 10 minutes. 4-iodo-1H-imidazole (145.5 mg, 0.75 mmol), (1-(tert-butoxycarbonyl)-1H-indol-2-yl)boronic acid (235.0 mg, 0.9 mmol) and Pd(PPh3)4 (86.7 mg, 75.0 μmol) were added followed by purging with nitrogen for an additional 2 minutes. The solution was heated at 85° C. over night. The solution was poured into water (20 mL) and the aqueous phase was extracted with ethyl acetate. The combined organic layers were washed with water (2×10 mL), brine and dried. The solvent was removed under reduced pressure and the crude residue was purified by column chromatography on silica gel using 10% MeOH/DCM as the eluent. The BOC protecting group was lost during the reaction sequence. Yield=37%. 1H NMR: 6.66 (s, 1H), 7.07-7.15 (m, 2H), 7.32 (s, 1H), 7.33 (d, 1H, J=7.8 Hz), 7.57 (d, 1H, J=7.5 Hz), 7.63 (s, 1H), 9.47 (s, 1H).

Provenance & Evidence