Dimethylformamide → HCID 89600926, compound

Participants

Reaction Conditions

Reaction Steps

A microwave vial was charged with 2-(4-bromo-2,6-dichloro-phenyl)-3-methoxy-5-(2-pyridylmethyl)cyclopent-2-en-1-one (90 mg, 0.21 mmol), caesium fluoride (CsF, 64 mg, 0.42 mmol), copper(I) iodide (CuI, 8 mg, 0.042 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (23 mg, 0.032 mmol), tributyl(prop-1-ynyl)stannane (83 mg, 0.25 mmol) and N,N-dimethylformamide (0.9 ml), sealed and heated at 120°C. under microwave irradiation for 30 minutes. Further caesium fluoride (32 mg, 0.21 mmol), copper(I) iodide (4 mg, 0.021 mmol), dichloro[1,1′-bis(diphenylphosphino)ferrocene]palladium(II) dichloromethane adduct (12 mg, 0.016 mmol) and tributyl(prop-1-ynyl)stannane (42 mg, 0.13 mmol) were added and the reaction heated at 120°C. under microwave irradiation for a further 30 minutes. The reaction was allowed to cool to room temperature, diluted with water (10 ml) and Et2O (10 ml) and filtered through Celite. The filtrate phases were separated and the aqueous phase extracted with further Et2O (2×10 ml). The combined organic extracts were washed with brine (10 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The crude product was dissolved in EtOAc, absorbed onto silica and purified by flash chromatography on silica using an EtOAc/isohexane gradient to give the desired product (26 mg, 32%). 1H NMR (400 MHz, CDCl3)δ ppm 8.50 (d, 1H), 7.60 (dd, 1H), 7.30 (2×s, 2×1H), 7.25 (d, 1H), 7.15 (dd, 1H), 3.75 (s, 3H), 3.40-3.35 (m, 1H), 3.20-3.10 (m, 1H), 3.00-2.90 (m, 1H), 2.85-2.80 (m, 2H), 2.05 (s, 3H).

Provenance & Evidence