Sodium Carbonate → HCID 19078391, compound

Participants

Reaction Steps

3-(2-Phthalimidoethyl)-1-(p-toluenesulfonyl)-5-(trifluoromethanesulfonyloxy)-1H-indole (Example 11) (71 mg, 0.12 mmol) was dissolved in 1,2-dimethoxymethane (10 mL). Tetrakis(triphenylphosphine) palladium (14 mg, 0.012 mmol) and lithium chloride (10 mg, 0.24 mmol) were added and the resulting solution was stirred under argon at room temperature for 20 minutes. Thiophene-2-boronic acid (20 mg, 0.15 mmol) and sodium carbonate (2M solution in water, 0.1 ml) were added and the resulting mixture was stirred under argon at reflux for 4 hours. After cooling to room temperature, the crude product mixture was poured into ethyl acetate (20 mL), washed with water (20 mL), dried over magnesium sulfate and evaporated under reduced pressure. The residue was chromatographed on silica gel using hexane/ethyl acetate (4:1) as eluent to provide 3-(2-phthalimidoethyl)-1-(p-toluenesulfonyl)-5-(2-thienyl)-1H-indole (62 mg, 96%) as a colorless oil. 1H NMR (CDCl3, 300 MHz) δ:-- 7.95 (d, J=8.9 Hz, 1H), 7.85-7.82 (A2 of A2B2 system, 2H), 7.80 (d, J=1.4 Hz, 1H), 7.73 (d, J=8.9 Hz, 2H), 7.72-7.69 (B2 of A2B2 system, 2H), 7.55 (dd, J=1.5 and 8.7 Hz, 1H), 7.46 (s, 1H), 7.29 (dd, J=1.2 and 3.5 Hz, 1H), 7.25 (dd, J=1.2 and 5.0 Hz, 1H), 7.19 (d, J=8.9 Hz, 2H), 7.07 (dd, J=3.5 and 5.0 Hz, 1H), 4.00 (t, J=7.4 Hz, 2H), 3.09 (t, J=7.4 Hz, 2H), 2.33 (s, 3H).

Provenance & Evidence