Dimethylformamide → HCID 44224890, compound

Participants

Reaction Conditions

Reaction Steps

Azepan-1-yl-(2-bromo-5-phenyl-thiophen-3-yl)-methanone (109 mg, 0.30 mmol) was dissolved in DMF (2 mL). Zinc cyanide (0.30 mmol) and tetrakis(triphenylphosphine) palladium (0) (0.15 mmol) were added and the reaction heated at 100° C. for 5 hours. The reaction mixture was cooled to ambient temperature, quenched with a 1:1 mixture of 5% aqueous sodium thiosulfate and 10% aqueous potassium carbonate. The resulting mixture was extracted with ethyl acetate, and the organic solvent separated and then evaporated. The residue was purified by HPLC, eluting with 50%-90% acetonitrile in water (0.1% formic acid) over 30 minutes. The fractions containing the desired product were concentrated under vacuum and freeze-dried to give the title compound (16 mg). LCMS m/z 311.10 [M+H]+ R.T.=11.43 min (Analytical Method 2). 1H NMR (400 MHz, CHCl3-d): δ 7.60 (m, 2H), 7.5 (m, 3H), 7.2 (s, 1H), 3.75 (t, 2H), 3.5 (t, 2H), 1.9 (m, 2H), 1.75-1.6 (m, 6H).

Provenance & Evidence