Sodium Carbonate → HCID 178482645, compound

Participants

Reaction Steps

A mixture of 16 (150 mg, 0.298 mmol), 4-iodoimidazole (86.7 mg, 0.447 mmol), dichlorobis(triphenylphosphine)palladium (II) (20.9 mg, 0.0298 mmol), LiCl (37.9 mg, 0.894 mmol), 1M aq. Na2CO3 (0.75 mL, 0.75 mmol) in toluene (1.8 mL) and EtOH (1.8 mL) was microwaved at 120° C. for 15 min. The reaction mixture was cooled, brine (3 mL) was added and the aqueous layer extracted with ethyl acetate (3×5 mL). Sorbent (HM-N, Jones Chromatography) was added, the solvent evaporated and the product purified by silicagel chromatography using MeOH:CH2Cl2 (3:97) (gradient elution) to give product 17 as a brown foam (111 mg, 84%); 1H NMR (400 MHz, CDCl3) δ 2.96 (s, 6H), 6.77 (d, J=8.8 Hz, 2H), 7.48-7.35 (m, 5H), 7.52 (t, J=7.6 Hz, 1H), 7.81 (s, 1H), 7.99 (s, 1H), 8.11 (d, J=7.5 Hz, 2H), 8.27 (d, J=2.0 Hz, 1H), 8.61 (d, J=2.1 Hz, 1H).

Provenance & Evidence