Dimethylformamide → HCID 18318477, compound

Participants

Reaction Conditions

Reaction Steps

3-(4-Bromobenzyl)-2-[4-[2-(1-pyrrolidinyl)ethoxy]-phenyl]benzo[b]thiophene (178 mg, 0.36 mmol) was dissolved in DMF (2.0 mL) and treated with pyrrolidine (0.3 mL). The solution was purged with carbon monoxide for 5 min at 80° C. before the catalyst dichlorobis(triphenylphosphine)pallidium (10 mg) was added. The reaction mixture was allowed to stir under a balloon of carbon monoxide at 80° C. for 4 h, then diluted with brine (30 mL) and extracted with EtOAc (20 mL×3). The combined organic layers were dried with sodium sulfate and concentrated. Chromotography with Et3N:MeOH:EtOAc (5:5:90) afforded the product (16 mg) along with recovered starting material (140 mg). FDMS m/e: found 511 (M+H+); 1H NMR (CDCl3): δ 7.97 (d, 1H), 7.57 (m, 1H), 7.55 (d, 2H), 7.50 (m, 1H), 7.40 (m, 1H), 7.39 (d, 2H), 7.24 (d, 2H), 7.03 (d, 2H), 4.40 (s, 2H), 4.28 (t, 2H), 3.76 (t, 2H), 3.57 (t, 2H), 3.10 (t, 2H), 2.82 (m, 4H), 2.01 (m, 4H), 1.98 (m, 4H).

Provenance & Evidence