Dichloromethane → HCID 23571181, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of the bromide from Step 2 (20 mg) in toluene (0.5 mL), ethanol (0.25 mL) and water (0.25 mL) were added 3-fluorophenylboronic acid (8 mg), potassium carbonate (26 mg) and [1,1′bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (3 mg). The mixture was heated in a microwave at 100° C. for 5 min. Additional catalyst was added and the mixture was heated at 100° C. for a further 10 min. The reaction mixture was poured into satd. NaHCO3(aq) and extracted with ethyl acetate (×2). The combined organic extracts were washed with brine, dried over Na2SO4 and concentrated. Chromatography on silica eluting with 25% ethyl acetate in hexane gave the title compound (5.5 mg, 27%). δ (1H, 400 MHz, CDCl3) 1.31–1.41 (2H, m), 1.71–1.77 (2H, m), 2.47–2.51 (2H, m), 2.72–2.84 (2H, m), 3.25–3.29 (2H, m), 3.45 (2H, s), 3.70 (2H, q, J=8.7 Hz), 4.93 (1H, s), 7.01–7.06 (1H, m), 7.18 (1H, d, J=7.8 Hz), 7.28–7.31 (1H, m), 7.37–7.41 (2H, m), 7.68 (1H, dd, J=7.8, 1.6 Hz), 7.73 (1H, d, J=1.2 Hz), 8.00 (1H, s); MS (ES+) 538 ([MH]+).

Provenance & Evidence